Highly enantioselective hydrogenation of exocyclic double bond of N-tosyloxazolidinones catalyzed by a neutral rhodium complex and its synthetic applications

Z Shen, X Lu, A Lei

Index: Shen, Zengming; Lu, Xiyan; Lei, Aiwen Tetrahedron, 2006 , vol. 62, # 39 p. 9237 - 9246

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Citation Number: 13

Abstract

A highly enantioselective synthesis of optically active N-tosyl-4-alkyl-1, 3-oxazolidin-2-ones based on the asymmetric hydrogenation of the trisubstituted exocyclic double bond of N- tosyl-4-alkylidene-1, 3-oxazolidin-2-ones under the catalysis of neutral [Rh (COD) Cl] 2 (COD= 1, 5-cyclooctadiene) and (S)-(+)-DTBM-SEGPHOS was developed. The utility of this highly enantioselective reaction was exemplified by the synthesis of optically active amino ...