催化学报

催化学报 ›› 2010, Vol. 31 ›› Issue (9): 1098-1102.DOI: 10.1016/S1872-2067(10)60106-4

• 研究论文 • 上一篇    下一篇

基于甲磺酰基的磺酰胺-氨醇作为催化醛的不对称炔基化反应新配体

金薇, 黄永波, 万伯顺   

  1. 中国科学院大连化学物理研究所, 辽宁大连 116023
  • 收稿日期:2010-09-30 出版日期:2010-09-30 发布日期:2014-01-25

Methylsulfonyl-Based Sulfamide-Amine Alcohol as a Ligand for Enantioselective Alkynylation of Aldehydes

JIN Wei, HUANG Yongbo, WAN Boshun*   

  1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
  • Received:2010-09-30 Online:2010-09-30 Published:2014-01-25

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摘要： 以商业易得的 (–)-麻黄碱、(+)-伪麻黄碱和各种手性氨醇为主要原料, 经过简单的两步反应, 合成了一系列基于甲磺酰基的磺酰胺-氨醇 (SAA) 配体, 并将其用于催化苯乙炔基锌对醛的不对称加成反应. 在没有 Ti(OiPr)4 等金属试剂的条件下, 配体表现出较好的不对称诱导能力, 取得了高达 83% ee.

关键词: 磺酰胺-氨醇配体, 不对称加成, 炔基化反应, 醛

Abstract: Chiral methylsulfonyl-based sulfamide-amine alcohol (SAA) ligands were synthesized from commercially available starting materials in two simple steps. Methylsulfonyl-based SAA ligands catalyzed the asymmetric alkynylation of various aldehydes using alkynylzinc to provide chiral propargyl alcohols with moderate to good enantioselectivity up to 83% ee.

Key words: sulfamide-amine alcohol, enantioselective addition, alkynylation, aldehyde