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NATURE CHEMISTRY | www.nature.com/naturechemistry 1 SUPPLEMENTARY INFORMATION DOI: 10.1038/NCHEM.1971 Contents 1 General Information SI-2 2 General Procedures SI-3 3 Synthesis of the starting materials SI-4 4 Electrophiles Screening SI-11 5 Reaction Products SI-12 6 Gram-scale arylation of 1f SI-37 7 NMR spectra and chiral HPLC/SFC/GC traces SI-38 Enantiospecific sp 2 -sp 3 coupling of secondary and tertiary boronic esters Amadeu Bonet, Marcin Odachowski, Daniele Leonori, Stephanie Essafi and Varinder K. Aggarwal School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK
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Page 1: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 2: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 3: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 4: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 5: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 6: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 7: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 8: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 9: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 10: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 11: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
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Page 22: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
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Page 40: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
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NATURE CHEMISTRY | www.nature.com/naturechemistry 68

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SI-68

(R)-3d 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

O

Ph

t-BuO2C

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 69

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SI-69

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

min10.5 11 11.5 12 12.5 13 13.5

mAU

0

100

200

300

400

500

600

700

DAD1 C, Sig=210,8 Ref=360,100 (AMADEU\AB445000.D)

11.

286

12.

148

min11 11.5 12 12.5 13 13.5

mAU

0

100

200

300

400

500

600

DAD1 C, Sig=210,8 Ref=360,100 (AMADEU\AB445003.D)

11.

353

12.

238

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 70

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SI-70

(R)-4a   1H NMR (400 MHz, CDCl3)

13C NMR (100 MHz, CDCl3)

S

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 71

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SI-71

Chiral HPLC traces: racemic

 

Chiral HPLC traces: enantioenriched

min0 10 20 30 40 50 60 70 80 90

mAU

0

0.5

1

1.5

2

2.5

DAD1 B, Sig=254,16 Ref=360,100 (MARTIN\MOC85-4.D)

Area: 633

.011

76

.57

6

Area: 660

.554

85

.77

2

min0 20 40 60 80 100

mAU

0

5

10

15

20

25

30

DAD1 B, Sig=254,16 Ref=360,100 (MARTIN\MOC91.D)

Area: 923

4.12

76

.37

5

Area: 210

.822

87

.10

5

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 72

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SI-72

(R)-5d   1H NMR (400 MHz, CDCl3)

13C NMR (100 MHz, CDCl3)

O

Ph

CO2t-Bu

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 73

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-73

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 74

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SI-74

(R)-6a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

N

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 75

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SI-75

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 76

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SI-76

6j 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

TBSOH

H

H H

H

N

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 77

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-77

(R)-7a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

OMeMeO

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 78

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-78

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 79

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SI-79

7i 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

HOH

H

H H

H

OMeMeO

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 80

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SI-80

(S)-7k 1H NMR (400 MHz, CDCl3)    

 

 13C NMR (100 MHz, CDCl3)

Ph

OMe

MeO

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 81

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SI-81

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 82

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SI-82

(S)-7l 1H NMR (400 MHz, CDCl3)    

13C NMR (100 MHz, CDCl3)

Ph

OMe

MeO

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 83

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-83

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

Chiral HPLC traces: enantioenriched + racemic

min0 2 4 6 8 10 12 14 16 18

mAU

0

50

100

150

200

250

300

350

400

DAD1 A, Sig=250,100 Ref=360,100 (MARTIN\MOD107R.D)

9.4

37

10.

963

min0 2 4 6 8 10 12 14 16 18

mAU

0

5

10

15

20

25

30

35

DAD1 A, Sig=250,100 Ref=360,100 (MARTIN\MOD165A1.D)

Area: 11

99.15

9.1

74

min0 2.5 5 7.5 10 12.5 15 17.5 20 22.5

mAU

0

100

200

300

400

500

DAD1 C, Sig=210,8 Ref=360,100 (MARTIN\MOC15000.D)

Area

: 814

4.78

9.4

69

Area

: 279

.214

10.

343

© 2014 Macmillan Publishers Limited. All rights reserved.

Page 84: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu

NATURE CHEMISTRY | www.nature.com/naturechemistry 84

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-84

(R)-8a 1H NMR (400 MHz, CDCl3)

13C NMR (100 MHz, CDCl3)

Me2N

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

Page 85: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu

NATURE CHEMISTRY | www.nature.com/naturechemistry 85

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-85

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 86

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-86

8j 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

TBSOH

H

H H

H

NMe2

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 87

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-87

(R)-9a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

MeO

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 88

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-88

Chiral SFC traces: racemic

Chiral SFC: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

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NATURE CHEMISTRY | www.nature.com/naturechemistry 89

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-89

(R)-10a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

Page 90: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu

NATURE CHEMISTRY | www.nature.com/naturechemistry 90

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

   

SI-90

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

Page 91: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 92: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 93: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 94: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
Page 95: SUPPLEMENTARY INFORMATION - Nature · SUPPLEMENTARY INFORMATION. DOI: 10.1038/NCHEM.1971 SI-1 . Enantiospecific sp. 2-sp. 3. coupling of secondary & tertiary boronic esters. Amadeu
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NATURE CHEMISTRY | www.nature.com/naturechemistry 96

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-96  

Chiral SFC traces for B(pin)-11k: racemic

Chiral HPLC traces for B(pin)-11k: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.


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