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

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.

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. 

Newly developed methylsulfonyl-based sulfamide-amine alcohol ligands, which were conveniently synthesized from commercially available starting materials in two simple steps, have been found to be effective ligands for the asymmetric alkynylation of aromatic aldehydes with up to 83% ee.Figure optionsDownload as PowerPoint slide