Scope and limitations of the scandium-catalyzed enantioselective addition of chiral allylboronates to aldehydes

被引：42

作者：

Gravel, M ^{[1
]}

Lachance, H ^{[1
]}

Lu, XS ^{[1
]}

Hall, DG ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Gunning Lemieux Chem Ctr, Edmonton, AB T6G 2G2, Canada

来源：

SYNTHESIS-STUTTGART | 2004年 / 08期

关键词：

allylations; chiral auxiliaries; crotylations; Lewis acids; scandium;

D O I：

10.1055/s-2004-822359

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scandium triflate catalyzes the addition of camphor-derived allyl-, methallyl-, and crotylboronates to aldehydes to provide homoallylic alcohols with excellent diastereo- and enantioselectivity. Aromatic, aliphatic, and propargylic aldehydes can be used successfully in this system. Additional advantages of the camphor-diol allylboronates are their ease of synthesis, their availability in both enantiomeric forms, and their stability towards silica gel chromatography. The usefulness of this methodology is further demonstrated by the gram-scale synthesis of various homoallylic alcohols of high enantiomeric excess and by the concise synthesis of the pheromone (4S)-2-methyloctan-4-ol.

引用

页码：1290 / 1302

页数：13

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