(-)-frontalin:: Synthesis using the catalytic enantioselective addition of dimethylzinc to a ketone

被引：64

作者：

Yus, M ^{[1
]}

Ramón, DJ ^{[1
]}

Prieto, O ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 15期

关键词：

asymmetric catalysis; enantioselectivity; C-C coupling; lithium; natural products;

D O I：

10.1002/ejoc.200300261

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective synthesis of (-)-frontalin involving an enantioselective nucleophilic 1,2-addition of dimethylzinc to a functionalized alpha,beta-unsaturated ketone, in the presence of titanium tetraisopropoxide and a substoichiometric amount of the chiral ligand 1,2-trans-bis(hydroxycamphor-sulfonamido)cyclohexane (HOCSAC, 2) as the key step, is described. The enantiomeric excess is as high as 89%. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

引用

页码：2745 / 2748

页数：4

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