Formation of optically active chromanes by catalytic asymmetric tandem oxa-Michael addition-Friedel-Crafts alkylation reactions

被引：75

作者：

van Lingen, HL

Zhuang, W

Hansen, T

Rutjes, FPJT

Jorgensen, KA

机构：

[1] Univ Nijmegen, Dept Organ Chem, NSRIM, NL-6525 ED Nijmegen, Netherlands

[2] Aarhus Univ, Dept Chem, Danish Natl Res Fdn, Ctr Catalysis, DK-8000 Aarhus, Denmark

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 11期

关键词：

D O I：

10.1039/b303353h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel tandem reaction involving an oxa-Michael addition, followed by a Friedel-Crafts alkylation has been developed. This catalytic tandem reaction, which provides facile and efficient access to optically active functionalised chromanes, proceeds under the influence of bisoxazoline-based catalysts to give diastereomerically pure products in enantioselectivities up to 81% and excellent yields. The optimisation studies, the scope of the reaction, and a model that on the basis of PM3 calculations predicts the outcome of the reaction will be detailed.

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页码：1953 / 1958

页数：6

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