Tetrahedron letters

Synthesis of pyrrolidines by anionic cyclization onto allylic ethers, alkynes and carboxylic groups

…, MMS Lang-Anderson, RE Rathmell, DJ Snowden

Index: Coldham, Iain; Lang-Anderson, Maria M.S.; Rathmell, Richard E.; Snowden, David J. Tetrahedron Letters, 1997 , vol. 38, # 43 p. 7621 - 7624

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Citation Number: 31

Abstract

Anionic cyclizations are becoming increasingly popular for the preparation of carbocyclic and heterocyclic ring systems.[1]We have found that the stannane 1, on transmetallation with butyllithium, gives the 3-substituted pyrrolidine products 2 after electrophilic quench.2, 3 and 4The intermediate α-amino-methyllithium cyclizes onto the unactivated alkene to give the 3-lithiomethylpyrrolidine, which can be trapped with electrophiles. We wished to ...