Graphical contents list
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iii Tetrahedron: Asymmetry Vol. 25, No. 1, 2014 Contents REPORT Julia–Kocienski olefination: a key reaction for the synthesis of macrolides pp 1–55 Bhaskar Chatterjee, Smritilekha Bera*, Dhananjoy Mondal This review is an overview of the Julia–Kocienski olefination for the formation of stereoselective C–C double bond in the synthesis of biologically active natural products, analogues, and building blocks containing macrocycles, in particular, macrolides. ARTICLES Diastereoselective synthesis of a highly functionalized cyclohexene embedded with a quaternary stereogenic centre by self Diels–Alder dimerization of a [3]dendralene attached to a ())-menthol auxiliary pp 57–62 Rekha Singh, Sunil K. Ghosh* Me2S=CH2 O P O O OCH2CF3 OCH2CF3 Ph 4-Br-C6H4CHO O O Ph Ph Ph Br Br O O O O Br Enantio- and diastereoselective hetero-Diels–Alder reactions between 4-methyl-substituted RawalÕs diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates: catalytic asymmetric synthesis of ())-cis-aerangis lactone pp 63–73 Yudai Watanabe, Naoyuki Shimada, Masahiro Anada*, Shunichi Hashimoto* Rh Rh O N N O O H Rh 2 ((S)-BPTPI) 4 OTBS Me2N Me + O R H 1. Rh2((S)-BPTPI)4 (3 mol %), CH2Cl2 2. DMAD, 0 °C 3. AcCl, –78 °C O Me R O O Me O (–)-cis-aerangis lactone >99% cis up to 98% ee (1E,3Z)/(1E,3E) = 74:26 Contents lists available at ScienceDirect Tetrahedron: Asymmetry journal homepage: www.elsevier.com/locate/tetasy
Transcript of Graphical contents list
iii
Tetrahedron: Asymmetry Vol. 25, No. 1, 2014
Contents
REPORT
Julia–Kocienski olefination: a key reaction for the synthesis of macrolides pp 1–55
Bhaskar Chatterjee, Smritilekha Bera*, Dhananjoy Mondal
This review is an overview of the Julia–Kocienski olefination for the formation of stereoselective C–C double bond in the synthesis of biologically active naturalproducts, analogues, and building blocks containing macrocycles, in particular, macrolides.
ARTICLES
Diastereoselective synthesis of a highly functionalized cyclohexene embedded with a quaternary stereogenic centreby self Diels–Alder dimerization of a [3]dendralene attached to a ())-menthol auxiliary
pp 57–62
Rekha Singh, Sunil K. Ghosh*
Me2S=CH2OP
O O
OCH2CF3OCH2CF3
Ph
4-Br-C6H4CHO O
O
Ph
Ph
Ph
Br
Br
O
O
OO
Br
Enantio- and diastereoselective hetero-Diels–Alder reactions between 4-methyl-substituted Rawal�s diene andaldehydes catalyzed by chiral dirhodium(II) carboxamidates: catalytic asymmetric synthesis of ())-cis-aerangis lactone
pp 63–73
Yudai Watanabe, Naoyuki Shimada, Masahiro Anada*, Shunichi Hashimoto*
Rh Rh
ON
N
O
O
H
Rh2((S)-BPTPI)4
OTBS
Me2N
Me
+ O R
H1. Rh2((S)-BPTPI)4
(3 mol %), CH2Cl2
2. DMAD, 0 °C3. AcCl, –78 °C O
Me
R
O
O
Me
O
(–)-cis-aerangis lactone
>99% cisup to 98% ee
(1E,3Z)/(1E,3E) = 74:26
Contents lists available at ScienceDirect
Tetrahedron: Asymmetry
journal homepage: www.elsevier .com/locate / tetasy
Tertiary amine-promoted enone aziridination: investigations into factors influencing enantioselective induction pp 74–86
Alan Armstrong*, Robert D.C. Pullin, Chloe R. Jenner, Klement Foo, Andrew J.P. White, James N. Scutt
O
R2
R1
O
R2
R1
N
>95:5 trans/cisupto 77% ee
HR3N*
DppONH2 O
Ph
N
OMe
NOH
HNH
+_
A concise synthesis of ())-lentiginosine via an anti,syn-oxazine pp 87–91
Gun-Woo Kim, Tian Jin, Jin-Seok Kim, Seok-Hwi Park, Kun-Hee Lee, Seong-Soo Kim, In-Soo Myeong, Won-Hun Ham*
N O
OTBS
Ph
TBSO
anti,syn-oxazine
N
H OH
OH
(-)-lentiginosine
10 steps
A facile synthesis of enantiopure 7-benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acid pp 92–97
Wen-Hua Chiou*, Yu-Min Chiang, Guei-Tang Chen
N
CO2H
Cbz
NCbz
N
O
O
O
R
NCbz
N
O
O
O
R
N Cbz
CO2H
N Cbz
CO2H
OH-
(±)-1
(-)-1
(+)-1
+
R = i-Pr, Me, i-Bu, (S)-sec-Bu
OH-
Organocatalytic asymmetric aza-Michael addition of pyrazole to chalcone pp 98–101
Pengfei Li*, Fang Fang, Ji Chen, Jun Wang*
Ar1 Ar2
O
+ NNH
R chiral primary amine NN
R
Ar1 A r2
OEt2O or 1, 4-dioxane
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OTHER CONTENTS
Stereochemistry abstracts pp A1–A19
Tetrahedron: Asymmetry Reports pp I–IV
Cumulative author index pp V
*Corresponding author
Available online at www.sciencedirect.com
ScienceDirect
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 Scopus®. Full text available onScienceDirect®
ISSN 0957-4166
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