Organocerium additions to proline-derived hydrazones: synthesis of enantiomerically enriched amines

…, JP Edwards, T Weber, DW Piotrowski

Index: Denmark, Scott E.; Edwards, James P.; Weber, Theodor; Piotrowski, David W. Tetrahedron Asymmetry, 2010 , vol. 21, # 9-10 p. 1278 - 1302

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Citation Number: 12

Abstract

The addition of organocerium reagents (from both organolithium and organomagnesium precursors) to chiral aldehyde hydrazones prepared from 1-aminoproline derivatives has been studied. The additions proceed in good yield and high diastereoselectivity and with good nucleophile (Me, n-Bu, i-Pr, t-Bu, Ph, etc.) and substrate scope (alkyl, alkenyl and aryl). The resulting hydrazines can be converted to amines by N–N bond cleavage through ...