Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation

…, KN Price, RE Rathmell, DJ Snowden, GP Vennall

Index: Coldham; Hufton; Price; Rathmell; Snowden; Vennall Synthesis, 2001 , # 10 p. 1523 - 1531

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Citation Number: 14

Abstract

Abstract Methods for the preparation of substituted homoallylic amines and their conversion to pyrrolidines or pyrrolizidines are described. N-Alkylation of a variety of homoallylic secondary amines with (tributylstannyl) methyl methanesulfonate and subsequent tin-lithium exchange, generates organolithium species that undergo intramolecular carbolithiation (anionic cyclization). High stereoselectivities in the cyclization, particularly for the ...