Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines
作者:Derek A. Cogan、Guangcheng Liu、Jonathan Ellman
DOI:10.1016/s0040-4020(99)00451-2
日期:1999.7
High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert-butanesulfinyl ketimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6)
对于有机金属试剂的1,2-增补高产量和高立体选择性的方法ñ -叔-butanesulfinyl醛亚胺(2)和Ñ -叔-butanesulfinyl酮亚胺(3)中描述。已证明将烷基,芳基,烯基和烯丙基碳负离子添加到具有不同空间和电子特性的各种亚胺中。亚磺酰胺产物(4和6)的酸性甲醇分解可提供高度对映体富集的α-支化和α,α-二支化胺。由于很容易从醛和酮中获得广泛的亚磺酰基亚胺,因此可以制备多种对映体富集的胺。