Synthesis

Enantioselectivity and diastereoselectivity in reductive radical cyclization reactions of 3-(ω-iodoalkylidene)-piperidin-2-ones

M Dressel, T Aechtner, T Bach

Index: Dressel, Martina; Aechtner, Tobias; Bach, Thorsten Synthesis, 2006 , # 13 p. 2206 - 2214

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Citation Number: 11

Abstract

Abstract The E-configurated 3-(ω-iodoalkylidene)-piperidin-2-ones 1a-e were prepared from the corresponding ω-tert-butyldimethylsilyloxyalkanals 5a-e by aldol condensation with N- tert-butyloxycarbonylpiperidone, subsequent silyl deprotection and iodo-dehydroxylation. In the presence of tributylstannane as the reducing agent and of triethylborane as the initiator the iodides underwent a reductive radical cyclization to the corresponding products rac-9a ...