Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines

Tin-lithium exchange allows the formation of alpha-amino-organolithium species that undergo anionic cyclization onto allylic ethers to give 3-alkenylpyrrolidines. The methodology has been applied to the synthesis of an advanced intermediate related to the natural product (-)-alpha-kainic acid.

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 1; no. 12; pp. 2111 - 2119
Main Authors Coldham, Price, KN, Rathmell, RE
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.06.2003
Subjects
Alkenes - chemical synthesis
Alkenes - chemistry
Chemistry
Chemistry, Organic
Cyclization
Kainic Acid - chemical synthesis
Lithium - chemistry
Organometallic Compounds - chemistry
Physical Sciences
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Science & Technology
Stereoisomerism
Tin - chemistry
ROUTE
(-)-KAINIC ACID
METHODOLOGY
STEREOSELECTIVITY
PYRROLIDINES
ANIONIC CYCLIZATION
(-)-ALPHA-KAINIC ACID
ALKYLLITHIUMS
DERIVATIVES
CYCLOPENTANES
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Summary:Tin-lithium exchange allows the formation of alpha-amino-organolithium species that undergo anionic cyclization onto allylic ethers to give 3-alkenylpyrrolidines. The methodology has been applied to the synthesis of an advanced intermediate related to the natural product (-)-alpha-kainic acid.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/b303670g