Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidines

Christoforos G. Kokotos; Varinder K. Aggarwal

doi:10.1039/b602226j

Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidines

Christoforos G. Kokotos, Varinder K. Aggarwal^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

51 Citations (Scopus)

Abstract

Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enandoselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.

Original language	English
Pages (from-to)	2156-2158
Number of pages	3
Journal	Chemical Communications
Issue number	20
DOIs	https://doi.org/10.1039/b602226j
Publication status	Published - 28 May 2006

Keywords

THROMBOXANE RECEPTOR ANTAGONIST
EPOXIDE OPENINGS
(+/-)-(5Z)-7-<3-ENDO-<(PHENYLSULFONYL)AMINO>BICYCLO<2.2.1>HEPT-2-EXO-YL>HEPTENO ACID
STEREOSELECTIVE-SYNTHESIS
TETRAHYDROPYRAN SYSTEMS
DERIVATIVES
6-ENDO
5-EXO
STEREOISOMERS
ACTIVATION

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@article{fc7035a10b5f461d947842bf09fcd3df,

title = "Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidines",

abstract = "Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enandoselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.",

keywords = "THROMBOXANE RECEPTOR ANTAGONIST, EPOXIDE OPENINGS, (+/-)-(5Z)-7-<3-ENDO-<(PHENYLSULFONYL)AMINO>BICYCLO<2.2.1>HEPT-2-EXO-YL>HEPTENO ACID, STEREOSELECTIVE-SYNTHESIS, TETRAHYDROPYRAN SYSTEMS, DERIVATIVES, 6-ENDO, 5-EXO, STEREOISOMERS, ACTIVATION",

author = "Kokotos, {Christoforos G.} and Aggarwal, {Varinder K.}",

year = "2006",

month = may,

day = "28",

doi = "10.1039/b602226j",

language = "English",

pages = "2156--2158",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "20",

}

TY - JOUR

T1 - Hemiaminals as substrates for sulfur ylides

T2 - Direct asymmetric syntheses of functionalised pyrrolidines and piperidines

AU - Kokotos, Christoforos G.

AU - Aggarwal, Varinder K.

PY - 2006/5/28

Y1 - 2006/5/28

N2 - Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enandoselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.

AB - Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enandoselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.

KW - THROMBOXANE RECEPTOR ANTAGONIST

KW - EPOXIDE OPENINGS

KW - (+/-)-(5Z)-7-<3-ENDO-<(PHENYLSULFONYL)AMINO>BICYCLO<2.2.1>HEPT-2-EXO-YL>HEPTENO ACID

KW - STEREOSELECTIVE-SYNTHESIS

KW - TETRAHYDROPYRAN SYSTEMS

KW - DERIVATIVES

KW - 6-ENDO

KW - 5-EXO

KW - STEREOISOMERS

KW - ACTIVATION

U2 - 10.1039/b602226j

DO - 10.1039/b602226j

M3 - Article (Academic Journal)

SN - 1359-7345

SP - 2156

EP - 2158

JO - Chemical Communications

JF - Chemical Communications

IS - 20

ER -

Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidines

Abstract

Keywords

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