Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles

K2CO3-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 SN2–conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselect...

Full description

Bibliographic Details
Main Authors: Heng, Yi Li, Chiba, Shunsuke, Tong, Benny Meng Kiat, Chen, Hui, Chong, Sin Yee
Other Authors: School of Physical and Mathematical Sciences
Format: Journal Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/96126
http://hdl.handle.net/10220/10606
_version_ 1826127981811073024
author Heng, Yi Li
Chiba, Shunsuke
Tong, Benny Meng Kiat
Chen, Hui
Chong, Sin Yee
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Heng, Yi Li
Chiba, Shunsuke
Tong, Benny Meng Kiat
Chen, Hui
Chong, Sin Yee
author_sort Heng, Yi Li
collection NTU
description K2CO3-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 SN2–conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner.
first_indexed 2024-10-01T07:17:24Z
format Journal Article
id ntu-10356/96126
institution Nanyang Technological University
language English
last_indexed 2024-10-01T07:17:24Z
publishDate 2013
record_format dspace
spelling ntu-10356/961262020-03-07T12:37:06Z Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles Heng, Yi Li Chiba, Shunsuke Tong, Benny Meng Kiat Chen, Hui Chong, Sin Yee School of Physical and Mathematical Sciences K2CO3-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 SN2–conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner. 2013-06-25T03:56:28Z 2019-12-06T19:26:08Z 2013-06-25T03:56:28Z 2019-12-06T19:26:08Z 2012 2012 Journal Article Tong, B. M. K., Chen, H., Chong, S. Y., Heng, Y. L., & Chiba, S. (2012). Formal [4 + 1]- and [5 + 1]-Annulation by an SN2–Conjugate Addition Sequence: Stereoselective Synthesis of Highly Substituted Carbocycles. Organic Letters, 14(11), 2826-2829. 1523-7060 https://hdl.handle.net/10356/96126 http://hdl.handle.net/10220/10606 10.1021/ol301044e en Organic letters © 2012 American Chemical Society.
spellingShingle Heng, Yi Li
Chiba, Shunsuke
Tong, Benny Meng Kiat
Chen, Hui
Chong, Sin Yee
Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles
title Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles
title_full Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles
title_fullStr Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles
title_full_unstemmed Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles
title_short Formal [4 + 1]- and [5 + 1]-annulation by an SN2–conjugate addition sequence : stereoselective synthesis of highly substituted carbocycles
title_sort formal 4 1 and 5 1 annulation by an sn2 conjugate addition sequence stereoselective synthesis of highly substituted carbocycles
url https://hdl.handle.net/10356/96126
http://hdl.handle.net/10220/10606
work_keys_str_mv AT hengyili formal41and51annulationbyansn2conjugateadditionsequencestereoselectivesynthesisofhighlysubstitutedcarbocycles
AT chibashunsuke formal41and51annulationbyansn2conjugateadditionsequencestereoselectivesynthesisofhighlysubstitutedcarbocycles
AT tongbennymengkiat formal41and51annulationbyansn2conjugateadditionsequencestereoselectivesynthesisofhighlysubstitutedcarbocycles
AT chenhui formal41and51annulationbyansn2conjugateadditionsequencestereoselectivesynthesisofhighlysubstitutedcarbocycles
AT chongsinyee formal41and51annulationbyansn2conjugateadditionsequencestereoselectivesynthesisofhighlysubstitutedcarbocycles