Tetrahedron letters

Stereoselective anionic cyclizations to pyrrolidines

I Coldham, R Hufton, RE Rathmell

Index: Coldham, Iain; Hufton, Richard; Rathmell, Richard E. Tetrahedron Letters, 1997 , vol. 38, # 43 p. 7617 - 7620

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Citation Number: 32

Abstract

Cyclization of α-amino-organolithiums onto unactivated alkenes results in the formation of 2, 4-disubstituted pyrrolidines with high selectivities in favour of the cis isomers. The use of the α-methylbenzyl chiral auxiliary on the nitrogen atom gives rise to 3-substituted pyrrolidines with up to 58% de Without the chiral auxiliary, enantioselectivities in the presence of (−)- sparteine are poor.© 1997 Elsevier Science Ltd.