Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis

Chuo Chen, Xiaodong Li, Stuart L. Schreiber

Research output: Contribution to journalArticle

252 Citations (Scopus)

Abstract

We report a new catalyst system that should enhance the use of enantioselective 1,3-dipolar cycloadditions of azomethine ylides with electronic-deficient olefins in the divergent pathways of diversity-oriented synthesis (DOS). The underlying reaction is of considerable interest in DOS because its stereospecificity enables stereochemical diversification of up to four tetrahedral centers on pyrrolidine rings. This new catalyst system extends the scope and selectivity of the azomethine ylide cycloaddition and is compatible with reagents used in a one-bead/one-stock solution technology platform for DOS.

Original languageEnglish (US)
Pages (from-to)10174-10175
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number34
DOIs
StatePublished - Aug 27 2003

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Cycloaddition
Cycloaddition Reaction
Alkenes
Catalysts
Catalyst selectivity
Technology
Olefins
azomethine
pyrrolidine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis. / Chen, Chuo; Li, Xiaodong; Schreiber, Stuart L.

In: Journal of the American Chemical Society, Vol. 125, No. 34, 27.08.2003, p. 10174-10175.

Research output: Contribution to journalArticle

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