Formal [4 + 1]- and [5 + 1]-annulation by an S N2-conjugate addition sequence: Stereoselective synthesis of highly substituted carbocycles

Benny Meng Kiat Tong; Hui Chen; Sin Yee Chong; Yi Li Heng; Shunsuke Chiba

doi:10.1021/ol301044e

Formal [4 + 1]- and [5 + 1]-annulation by an S _N2-conjugate addition sequence: Stereoselective synthesis of highly substituted carbocycles

Benny Meng Kiat Tong, Hui Chen, Sin Yee Chong, Yi Li Heng, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

K ₂CO ₃-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S _N2-conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner.

Original language	English
Pages (from-to)	2826-2829
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	11
DOIs	https://doi.org/10.1021/ol301044e
Publication status	Published - Jun 1 2012
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol301044e

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title = "Formal [4 + 1]- and [5 + 1]-annulation by an S N2-conjugate addition sequence: Stereoselective synthesis of highly substituted carbocycles",

abstract = "K 2CO 3-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S N2-conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner.",

author = "Tong, \{Benny Meng Kiat\} and Hui Chen and Chong, \{Sin Yee\} and Heng, \{Yi Li\} and Shunsuke Chiba",

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T2 - Stereoselective synthesis of highly substituted carbocycles

AU - Tong, Benny Meng Kiat

AU - Chen, Hui

AU - Chong, Sin Yee

AU - Heng, Yi Li

AU - Chiba, Shunsuke

PY - 2012/6/1

Y1 - 2012/6/1

N2 - K 2CO 3-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S N2-conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner.

AB - K 2CO 3-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S N2-conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner.

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Formal [4 + 1]- and [5 + 1]-annulation by an S _N2-conjugate addition sequence: Stereoselective synthesis of highly substituted carbocycles

Abstract

ASJC Scopus Subject Areas

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