Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines

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• 作者：Cogan ; Derek A. ; Liu ; Guangcheng ; Ellman ; Jonathan
• 关键词：Amines ; Asymmetric reactions ; Diastereoselection ; Imines ; Sulfinamides
• 刊名：Tetrahedron
• 出版年：1999
• 出版时间：July 16, 1999
• 年：1999
• 卷：55
• 期：29
• 页码：8883-8904
• 全文大小：1.14 M

文摘

High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) 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) delivers highly enantioenriched α-branched and α,α-dibranched amines. Since a broad range of sulfinyl imines are easily accessible from aldehydes and ketones, a wide variety of enantioentriched amines may be prepared.