Asymmetric synthesis of diverse alpha,alpha-diarylmethylamines via aryl Grignard additions to chiral N-2,4,6-triisopropylbenzenesulfinylimines

作者：Han Zhengxu^*; Busch Robert; Fandrick Keith R; Meyer Angelica; Xu Yibo; Krishnamurthy Dhileep K; Senanayake Chris H

来源：Tetrahedron, 2011, 67(37): 7035-7041.

DOI：10.1016/j.tet.2011.07.019

• Chiral sulfinamide
• Sulfinylimine
• Chiral diarylmethylamines
• Asymmetric synthesis

A mild method has been developed for the asymmetric synthesis of a variety of chiral diarylmethylamines via the addition of aryl Grignard reagents to chiral N-2,4,6-triisopropylbenzenesulfinylimines in high yields and high diastereoselectivities. Higher stereoselectivity was obtained for most of the examples studied when the reactions are performed at ambient temperature as compared to cryogenic conditions. N-2,4,6-Triisopropylbenzenesulfinamide was shown to be the optimal chiral auxiliary as it provided higher diastereoselectivities when compared to the more commonly employed tert-butanesulfinamide or p-toluenesulfinamide in the synthesis of diarylmethylamine synthons. A rationale for the improved selectivity derived from the triisopropylbenzyl auxiliary is presented.

• 出版日期2011-9-16