Tetrahedron: Asymmetry

Stereocontrolled synthesis of conformationally restricted enantiopure triols and dihydroxy acids based on the norbornane framework

…, ET Vilar, AG Fraile, P Martı́nez-Ruiz

Index: Garcia Martinez, Antonio; Teso Vilar, Enrique; Garcia Fraile, Amelia; Martinez-Ruiz, Paloma Tetrahedron Asymmetry, 2005 , vol. 16, # 13 p. 2329 - 2332

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Abstract

The synthesis of chiral, rigid analogues of glycerol and cyclitols has been achieved by means of the stereocontrolled reduction of chiral bridgehead-substituted camphorquinones. This simple and easy procedure exclusively affords dihydroxy derivatives with a 2, 3-cis-exo- configuration. The employment of different hydrides has also allowed the synthesis of enantiopure 2, 3-dihydroxy carboxylic acids with high diastereoselectivity.