Boron-mediated aldol reaction of carboxylic esters: Complementary anti- and syn-selective asymmetric aldol reactions

被引：84

作者：

Inoue, T

Liu, JF

Buske, DC

Abiko, A ^{[1
]}

机构：

[1] Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 6068585, Japan

[2] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

D O I：

10.1021/jo0257896

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The boron-mediated aldol reaction of carboxylic esters is described in detail. Contrary to the general belief that carboxylic esters are inert under the condition of the boron enolate formation, propionate esters are enolized with certain combinations of a boron triflate and an amine. More importantly, the stereochemical course of the aldol reaction can be controlled by the judicious selection of the enolization reagents. Treatment of propionate esters with c-Hex(2)BOTf and triethylamine produces anti-aldol products, and that with Bu2BOTf and diisopropylethylamine gives syn-aldol products selectively after reaction with aldehydes. Complementary anti- and syn-selective asymmetric aldol reactions with structurally related, readily available chiral norephedrine-derived propionate esters are developed.

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页码：5250 / 5256

页数：7

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