iii Tetrahedron: Asymmetry Vol. 24, Nos. 2–3, 2013 Contents ARTICLES Response surface methodology as an optimization strategy for the light-controlled asymmetric hydrogenation of 4-(trimethylsilyl)-3-butyn-2-one by photosynthetic bacteria pp 81–88 Rui-Hu*, Yun-Sheng Xu, Dong-Xu Shao, Meng-Liang Wang Thermal and Sc(OTf) 3 catalyzed 1,3-dipolar cycloaddition of open-chain nitrones to a,b-unsaturated lactones: combined experimental and computational studies pp 89–103 Marcin S ´ nie _ zek, Sebastian Stecko*, Irma Panfil, Bartłomiej Furman, Zofia Urban ´ czyk-Lipkowska, Marek Chmielewski Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes pp 104–107 Qing-Lu Zhao, Xiao Miao, Lai-Lai Wang* MeOOC COOMe COOH n BuO MeO COOH n BuO MeO MeOOC COOMe 98% ee (ligand 1d) 75% ee (ligand 3b) O O O O O O O O O O P O O P O O ligand 1d OMe P O O P O O ligand 3b [Rh(cod) 2 ]BF 4 , ligand H 2 , CH 2 Cl 2 , r.t. H Me 10 11 12 13 Contents lists available at SciVerse ScienceDirect Tetrahedron: Asymmetry journal homepage: www.elsevier.com/locate/tetasy
Transcript
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Tetrahedron: Asymmetry Vol. 24, Nos. 2–3, 2013
Contents
ARTICLES
Response surface methodology as an optimization strategy for the light-controlled asymmetric hydrogenation of4-(trimethylsilyl)-3-butyn-2-one by photosynthetic bacteria
pp 81–88
Rui-Hu*, Yun-Sheng Xu, Dong-Xu Shao, Meng-Liang Wang
Thermal and Sc(OTf)3 catalyzed 1,3-dipolar cycloaddition of open-chain nitrones to a,b-unsaturated lactones: combinedexperimental and computational studies
pp 89–103
Marcin Snie _zek, Sebastian Stecko*, Irma Panfil, Bartłomiej Furman, Zofia Urbanczyk-Lipkowska, Marek Chmielewski
Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes pp 104–107
Qing-Lu Zhao, Xiao Miao, Lai-Lai Wang*
MeOOCCOOMe
COOHnBuO
MeO
COOHnBuO
MeO
MeOOCCOOMe
98% ee (ligand 1d)
75% ee (ligand 3b)
O OOO
OO
OO
OOP
O
OP
O
O
ligand 1d
OMe
PO
O
PO
Oligand 3b
[Rh(cod)2]BF4, ligandH2, CH2Cl2, r.t.
HMe
10 11
1213
Contents lists available at SciVerse ScienceDirect
Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing along aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion
Polymer-supported LL-prolinol-based catalysts for the enantioselective addition of dialkylzinc reagents toN-(diphenylphosphinyl)imines
pp 116–120
Raquel Almansa, Juan F. Collados, David Guijarro*, Miguel Yus*
R H
NP
+ R'2Zn
i,
ii, separation
iii, NH4Cl (aq.)R R'
HNP
(ee up to 88%)
NOH
O
PhPh
O
PhPh
(1 equiv)
A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F pp 121–133
Miroslava Martinková*, Jozef Gonda, Alena Uhríková, Jana Špaková Raschmanová, Mária Vilková, Beáta Oroszová
5 5CO2H
OH
ClH.H2N
HOO
mycestericin G
OOO
HNO
O
5 5
OHOH
ClH.H2N CO2HO
ent-mycestericin F
O O
CHOBnN
OO
OH OH
ClH.H2N COOH5 5
O
mycestericin F
and/or
Organocatalytic asymmetric cross-aldol reaction of 2-chloroethoxy acetaldehyde: diversity-oriented synthesis of chiralsubstituted 1,4-dioxanes and morpholines
pp 134–141
Rajiv T. Sawant, Joanne Stevenson, Luke R. Odell, Per I. Arvidsson*
OTBSO2N
O
BnN
OH
O
X
O2N
X=NBn, 91% eeX= NnBu, 97% eeX= O, 95% ee
16, CH3CN:H2O, rt, 3 d
then NaBH4, MeOH, 0°C, 1 h
O
Ar H +Ar
OH
O
OH
OCl
H
O
Clee up to 98%de up to 7.3:1
94% ee
iv
Lipase-catalyzed asymmetric acylation in the chemoenzymatic synthesis of furan-based alcohols pp 142–150
Piia Hara, Mihaela-Claudia Turcu, Riku Sundell, Monica To+a, Csaba Paizs, Florin-Dan Irimie, Liisa T. Kanerva*
OR1
OH
OR1
O
OR2
OR1
OH
rac-2a-h (S)-2a-h (R)-3a-h
+OR1
OH
(R)-2a and c
R2CO2CH=CH2
CAL-B
CAL-B
R3OH
Asymmetric intramolecular C–H insertion of sulfonyldiazoacetates catalyzed by Rh(II) pp 151–155
Christian S. Jungong, Alexei V. Novikov*
O2S COOR Rh2(L)4
rt, CH2Cl2N2
O2S COOR
up to 90% de
Regioselective epoxide opening of epoxyamides derived from DD-glucose. Cyclization approaches to azepanes pp 156–163
Noe Oña, Antonio Romero-Carrasco, M. Soledad Pino-González*
O
O
O
O
OBn
CO
R2N
NaN3
DMF, AcOH cat.
R = Et, Bn, Me
OH
O
O
O
OBnN3
CO
R2NHN
HO
HO OH
OH
HO
R = Et, Bn, Me
OTHER CONTENTS
Stereochemistry abstracts pp A17–A35
Cumulative author index p I
*Corresponding author
v
Available online at www.sciencedirect.com
Indexed/Abstracted in: Beilstein, BIOSIS Previews, Chemical Abstracts, Current Contents: Physical, Chemical and EarthSciences, Derwent Biotechnology Abstracts, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, PASCAL, ResearchAlert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus®. Full text availableon SciVerse ScienceDirect®
