Chemical & Pharmaceutical Bulletin 2002-10-01

Synthesis of optically active organoantimony compounds having an (S)-alpha-methylbenzyldimethylamine group and its evaluation for asymmetric reaction.

Shuji Yasuike, Satoru Okajima, Jyoji Kurita

Index: Chem. Pharm. Bull. 50(10) , 1404-6, (2002)

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Abstract

Novel, enantiomerically pure organoantimony compounds having a C-chiral amine moiety, (S)-(alpha-methyl-2-di-p-tolylstibanobenzyl)dimethylamine [AMSb] (2) and its (eta(6)-arene)chromium complex [AMSb-Cr(CO)(3)] (4), were prepared from common (S)-(alpha-methylbenzyl)dimethylamine (1) via its ortho-lithiated intermediates in short steps. The catalytic activity and enantioselectivity of the ligands 2 and 4 for asymmetric reaction are evaluated, and the optically active (eta(6)-arene)chromium complex 4 has been shown to be an effective ligand for rhodium-catalyzed asymmetric hydrosilylation of ketones.