Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines

Jing Lin; Wing Hong CHAN; Albert W M LEE; Wai Yeung WONG; Pei Qiang Huang

doi:10.1016/S0040-4039(00)00278-1

Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines

Jing Lin, Wing Hong CHAN^*, Albert W M LEE, Wai Yeung WONG, Pei Qiang Huang

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

10 Citations (Scopus)

Abstract

Diastereoselective alkylation of N-acylnorbornene sultams 2 afforded a variety of enantiomerically pure products 3a-3e. Reduction with LiAlH₄ (LAH) followed by ditosylation furnished chiral 1,4-ditosylates 5a-5e which underwent a cyclization reaction with primary amines to afford chiral 1,3- and 1,3,4-substituted pyrrolidines. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	2949-2951
Number of pages	3
Journal	Tetrahedron Letters
Volume	41
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4039(00)00278-1
Publication status	Published - 15 Apr 2000

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

User-Defined Keywords

Asymmetric synthesis
Cyclization
Pyrrolidines
Sultams

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10.1016/S0040-4039(00)00278-1

Cite this

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title = "Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines",

abstract = "Diastereoselective alkylation of N-acylnorbornene sultams 2 afforded a variety of enantiomerically pure products 3a-3e. Reduction with LiAlH4 (LAH) followed by ditosylation furnished chiral 1,4-ditosylates 5a-5e which underwent a cyclization reaction with primary amines to afford chiral 1,3- and 1,3,4-substituted pyrrolidines. (C) 2000 Elsevier Science Ltd.",

keywords = "Asymmetric synthesis, Cyclization, Pyrrolidines, Sultams",

author = "Jing Lin and CHAN, {Wing Hong} and LEE, {Albert W M} and WONG, {Wai Yeung} and Huang, {Pei Qiang}",

note = "Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University (FRG/98-99/II-11) and the Croucher Foundation for providing a Visitorship for P. Q. Huang are gratefully acknowledged. ",

year = "2000",

month = apr,

day = "15",

doi = "10.1016/S0040-4039(00)00278-1",

language = "English",

volume = "41",

pages = "2949--2951",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "16",

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TY - JOUR

T1 - Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines

AU - Lin, Jing

AU - CHAN, Wing Hong

AU - LEE, Albert W M

AU - WONG, Wai Yeung

AU - Huang, Pei Qiang

N1 - Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University (FRG/98-99/II-11) and the Croucher Foundation for providing a Visitorship for P. Q. Huang are gratefully acknowledged.

PY - 2000/4/15

Y1 - 2000/4/15

N2 - Diastereoselective alkylation of N-acylnorbornene sultams 2 afforded a variety of enantiomerically pure products 3a-3e. Reduction with LiAlH4 (LAH) followed by ditosylation furnished chiral 1,4-ditosylates 5a-5e which underwent a cyclization reaction with primary amines to afford chiral 1,3- and 1,3,4-substituted pyrrolidines. (C) 2000 Elsevier Science Ltd.

AB - Diastereoselective alkylation of N-acylnorbornene sultams 2 afforded a variety of enantiomerically pure products 3a-3e. Reduction with LiAlH4 (LAH) followed by ditosylation furnished chiral 1,4-ditosylates 5a-5e which underwent a cyclization reaction with primary amines to afford chiral 1,3- and 1,3,4-substituted pyrrolidines. (C) 2000 Elsevier Science Ltd.

KW - Asymmetric synthesis

KW - Cyclization

KW - Pyrrolidines

KW - Sultams

UR - http://www.scopus.com/inward/record.url?scp=0342369344&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)00278-1

DO - 10.1016/S0040-4039(00)00278-1

M3 - Journal article

AN - SCOPUS:0342369344

SN - 0040-4039

VL - 41

SP - 2949

EP - 2951

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines

Abstract

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