N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines

被引：801

作者：

Ellman, JA ^{[1
]}

Owens, TD ^{[1
]}

Tang, TP ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2002年 / 35卷 / 11期

关键词：

D O I：

10.1021/ar020066u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-tert-Butanesulfinyl aldimines 3 and ketimines 4 are exceedingly versatile Intermediates for the asymmetric synthesis of amines. The N-tert-butanesulfinyl amines are prepared in high yields by condensing enantiomerically pure tert-butanesulfinamide 1, which is readily available in either configuration, with a wide range of aldehydes and ketones. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment of the product with acid. A wide range of highly enantioenriched amines, including alpha-branched and alpha,alpha-dibranched amines, alpha- and beta-amino acids, 1,2- and 1,3-amino alcohols, and alpha-trifluoromethyl amines, are efficiently synthesized using this methodology. In addition, N-tert-butanesulfinyl imine derivatives provide a new family of ligands for asymmetric catalysis.

引用

页码：984 / 995

页数：12

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