Tetrahedron

A flexible enantioselective approach to 3, 4-dihydroxyprolinol derivatives by SmI 2-mediated reductive coupling of chiral nitrone with ketones/aldehydes

HK Zhang, SQ Xu, JJ Zhuang, JL Ye, PQ Huang

Index: Zhang, Hong-Kui; Xu, Shou-Qiang; Zhuang, Jia-Jia; Ye, Jian-Liang; Huang, Pei-Qiang Tetrahedron, 2012 , vol. 68, # 33 p. 6656 - 6664

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Citation Number: 10

Abstract

A flexible enantioselective approach to polyhydroxylated prolinol derivatives was described, which is based on the samarium diiodide-mediated reductive coupling of the chiral nitrone (3S, 4R)-8, derived from d-isoascorbic acid with aldehydes/ketones. Thereby, polyhydroxyprolinol derivatives 9a–e and 9h–j were obtained from aromatic ketones and aliphatic aldehydes in good to excellent yields of 65–91%. These reductive ...