Diastereoselectivity Control of the Radical Carboazidation of Substituted Methylenecyclohexanes

…, P Schär, P Renaud, K Schenk

Index: Cren, Sylvaine; Schar, Pascal; Renaud, Philippe; Schenk, Kurt Journal of Organic Chemistry, 2009 , vol. 74, # 8 p. 2942 - 2946

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Citation Number: 21

Abstract

A systematic study of the diastereoselectivity of the radical carboazidation of methylenecyclohexane derivatives is presented. Several substitution patterns leading to a high level of stereocontrol have been identified. Axial attack is the preferred reaction pathway for cyclohexyl radicals, and excellent stereoselectivities can be obtained by introducing an axial substitutent at position 2. In this case, a second equatorial substituent ...