Tetrahedron

Asymmetric ring cleavage reaction with a combination of optically active cycloalkane-1, 2-diol and Lewis acid: application to formal synthesis of (−)-alloyohimbane and …

…, E Toyofuku, Y Demizu, O Yoshida, K Nakazawa…

Index: Tanaka, Masakazu; Toyofuku, Eiji; Demizu, Yosuke; Yoshida, Osamu; Nakazawa, Koichi; Sakai, Kiyoshi; Suemune, Hiroshi Tetrahedron, 2004 , vol. 60, # 10 p. 2271 - 2281

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Citation Number: 7

Abstract

Asymmetric ring cleavage reaction of meso-carbobicyclic ketones by a combination of benzaldehyde, chiral cycloalkane-1, 2-diol, and Lewis acid gave optically active styrenyl esters of 26–69% ee in moderate yield. The ring cleavage reaction could be applied to the construction of adjacent chiral quaternary carbons, and also to the formal synthesis of natural alkaloid (−)-alloyohimbane.