Highly Stereoselective Synthesis of Terminal Chloro-Substituted Propargylamines and Further Functionalization

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• 作者：Savannah Jordan ; Samuel A. Starks ; Michael F. Whatley ; Mark Turlington
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：October 2, 2015
• 年：2015
• 卷：17
• 期：19
• 页码：4842-4845
• 全文大小：291K
• ISSN：1523-7052

文摘

The highly stereoselective addition of lithiated chloroacetylene, derived in situ from cis-1,2-dichloroethene and methyl lithium, to Ellman chiral N-tert-butanesulfinyl imines is reported. The reaction proceeds in high yield (up to 98%) and with excellent diastereoselectivity (up to >20:1) for a variety of aryl, heteroaromatic, alkyl, and 伪,尾-unsaturated imine substrates. Transformations of the terminal chloro-substituted propargylamine products are described in which lithium鈥揾alogen exchange yields nucleophilic acetylides that can be quenched to yield terminal alkynes or intercepted by carbon electrophiles.