Stereoselective addition of sulfone carbanions to C=N: A critical dependence on the stability and reactivity of the amide anions in MIRC reactions

Alfred Hassner; Diana Usak; Ramaiah Kumareswaran; Oded Friedman

doi:10.1002/ejoc.200300781

Stereoselective addition of sulfone carbanions to C=N: A critical dependence on the stability and reactivity of the amide anions in MIRC reactions

Alfred Hassner, Diana Usak, Ramaiah Kumareswaran, Oded Friedman

Department of Chemistry

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

Abstract

A procedure was developed for the selective synthesis of functionalized 4-methylenepyrrolidines by tuning the electron-withdrawing group (ArSO ₂, COOEt, ArSO) attached to the acceptor imine nitrogen atom during addition of allyl sulfone carbanions. Sulfone carbanion additions to 2H-azirines were also examined.

Original language	English
Pages (from-to)	2421-2426
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	11
DOIs	https://doi.org/10.1002/ejoc.200300781
State	Published - 24 May 2004

Keywords

Cyclization
Diastereoselectivity
Imines
Pyrrolidines

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10.1002/ejoc.200300781

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AU - Kumareswaran, Ramaiah

AU - Friedman, Oded

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KW - Diastereoselectivity

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KW - Pyrrolidines

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Stereoselective addition of sulfone carbanions to C=N: A critical dependence on the stability and reactivity of the amide anions in MIRC reactions

Abstract

Keywords

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