A synthetic strategy to pyrrolidines and piperidines based on cyclization of α-sulfinyl carbanions

Wissawat Sakulsaknimitr; Chutima Kuhakarn; Patoomratana Tuchinda; Vichai Reutrakul; Manat Pohmakotr

doi:10.3998/ark.5550190.0010.c07

A synthetic strategy to pyrrolidines and piperidines based on cyclization of α-sulfinyl carbanions

Wissawat Sakulsaknimitr
, Chutima Kuhakarn
, Patoomratana Tuchinda
, Vichai Reutrakul
, Manat Pohmakotr

Department of Chemistry

Mahidol University

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

2 Citations (Scopus)

Abstract

A general synthetic strategy for the preparation of pyrrolidines, piperidines and their unsaturated analogs is described, which involves intramolecular cyclization of α-sulfinyl carbanions onto the carbonyl group of the readily prepared N-phenylsulfinylpropyl- or N- phenylsulfinylbutylamides, followed by reductive desulfurization or sulfoxide elimination of the resulting cyclized products.

Original language	English
Pages (from-to)	81-97
Number of pages	17
Journal	Arkivoc
Volume	2009
Issue number	12
DOIs	https://doi.org/10.3998/ark.5550190.0010.c07
Publication status	Published - 2009

Keywords

Intramolecular cyclization
Piperidines
Pyrrolidines
α-Sulfinyl carbanion

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10.3998/ark.5550190.0010.c07

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abstract = "A general synthetic strategy for the preparation of pyrrolidines, piperidines and their unsaturated analogs is described, which involves intramolecular cyclization of α-sulfinyl carbanions onto the carbonyl group of the readily prepared N-phenylsulfinylpropyl- or N- phenylsulfinylbutylamides, followed by reductive desulfurization or sulfoxide elimination of the resulting cyclized products.",

keywords = "Intramolecular cyclization, Piperidines, Pyrrolidines, α-Sulfinyl carbanion",

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T1 - A synthetic strategy to pyrrolidines and piperidines based on cyclization of α-sulfinyl carbanions

AU - Sakulsaknimitr, Wissawat

AU - Kuhakarn, Chutima

AU - Tuchinda, Patoomratana

AU - Reutrakul, Vichai

AU - Pohmakotr, Manat

PY - 2009

Y1 - 2009

N2 - A general synthetic strategy for the preparation of pyrrolidines, piperidines and their unsaturated analogs is described, which involves intramolecular cyclization of α-sulfinyl carbanions onto the carbonyl group of the readily prepared N-phenylsulfinylpropyl- or N- phenylsulfinylbutylamides, followed by reductive desulfurization or sulfoxide elimination of the resulting cyclized products.

AB - A general synthetic strategy for the preparation of pyrrolidines, piperidines and their unsaturated analogs is described, which involves intramolecular cyclization of α-sulfinyl carbanions onto the carbonyl group of the readily prepared N-phenylsulfinylpropyl- or N- phenylsulfinylbutylamides, followed by reductive desulfurization or sulfoxide elimination of the resulting cyclized products.

KW - Intramolecular cyclization

KW - Piperidines

KW - Pyrrolidines

KW - α-Sulfinyl carbanion

UR - https://www.scopus.com/pages/publications/77953193685

U2 - 10.3998/ark.5550190.0010.c07

DO - 10.3998/ark.5550190.0010.c07

M3 - Article

AN - SCOPUS:77953193685

SN - 1551-7012

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SP - 81

EP - 97

JO - Arkivoc

JF - Arkivoc

IS - 12

ER -

A synthetic strategy to pyrrolidines and piperidines based on cyclization of α-sulfinyl carbanions

Abstract

Keywords

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