Optically active naphthohydroquinone and naphthoquinone tricarbonyl chromium complexes via diastereoselective benzannulation with sec alcohol auxiliaries

被引：46

作者：

Dotz, KH

Stinner, C

机构：

[1] Inst. fur Org. Chem. und Biochem., Rheinischen Friedrich-Wilhelms-Univ., D-53121 Bonn

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(97)00142-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric benzannulation of optically active aryl or vinyl (alkoxy)carbene chromium complexes bearing chiral sec. alcohol auxiliaries with 3,3-dimethyl-1-butyne proceeds with moderate to high diastereoselectivities. The best results are obtained with (-)- and (+)-menthol derivatives. The stereoselectivity depends on the unsaturated carbene substituent and the solvent used. Enantiopure S-5-10-eta(6)-tricarbonyl-(2-tert.-butyl-1,4-naphthoquinone)chromium 25 was synthesized by intramolecular haptotropic migration of the tricarbonyl chromium fragment within the benzannulation product followed by deprotection and oxidation. (C) 1997 Elsevier Science Ltd.

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页码：1751 / 1765

页数：15

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