Nonenzymatic Enantioselective Monoacetylation of Prochiral 2-Protectedamino-2-alkyl-1,3-propanediols Utilizing a Chiral Sulfonamide−Zn Complex Catalyst
Organic Letters2007Vol. 9(3), pp. 509–512
Citations Over TimeTop 20% of 2007 papers
Takashi Honjo, Michiyasu Nakao, Shigeki Sano, Motoo Shiro, Kentaro Yamaguchi, Yoshihisa Sei, Yoshimitsu Nagao
Abstract
[structure: see text] Treatment of a chiral sulfonamide with Et(2)Zn gave quantitatively its Zn complex and then the structure was determined by X-ray crystallographic analysis. Reaction of prochiral N-Boc-2-amino-2-alkyl-1,3-propanediols with Ac(2)O in the presence of 5 mol % of chiral sulfonamide-Zn complex catalyst afforded the corresponding chiral monoacetyl products in 70-92% yields with 70-88% ee values. The proposed mechanism for the catalytic monoacetylation of a prochiral 1,3-propanediol was presented on the basis of CSI-MS analysis.
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