Boron-mediated aldol reaction of carboxylic esters

被引：67

作者：

Abiko, A ^{[1
]}

机构：

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

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2004年 / 37卷 / 06期

关键词：

D O I：

10.1021/ar030249w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This Account outlines the unique features of the boron-mediated aldol reaction of carboxylic esters, which include (i) facile isomerization of E-enolate to Z-enolate and (ii) formation of a doubly borylated enolate upon enolization of acetate esters. The first carbon-bound boron enolates were spectroscopically characterized, and they appeared to be responsible for these unique properties. Furthermore, complementary anti- and syn-selective boron-mediated asymmetric aldol reactions of chiral propionate esters have been developed. A novel double aldol reaction of acetate esters has been discovered, and a plausible mechanism of the double aldol reaction is proposed.

引用

页码：387 / 395

页数：9

共 47 条

[1] Mechanism of the double aldol reaction: The first spectroscopic characterization of a carbon-bound boron enolate derived from carboxylic esters
Abiko, A
Inoue, T
Masamune, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (36) : 10759 - 10764
[2] Boron-mediated double aldol reaction of carboxylic esters
Abiko, A
Liu, JF
Buske, DC
Moriyama, S
Masamune, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) : 7168 - 7169
[3] The first doubly borylated enolate as an intermediate of the double aldol reaction
Abiko, A
Inoue, T
Furuno, H
Schwalbe, H
Fieres, C
Masamune, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) : 4605 - 4606
[4] The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters
Abiko, A
Liu, JF
Masamune, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) : 2586 - 2587
[5] Concerning the boron-mediated aldol reaction of carboxylic esters
Abiko, A
Liu, JF
Masamune, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) : 2590 - 2591
[6] Abiko A., 2002, ORG SYNTH, V79, P109
[7] [Anonymous], 1997, ORG REACT
[8] BRAUN M, 1996, STEREOSELECTIVE SYNT, V3, P1603
[9] Braun M., 1992, ADV CARBANION CHEM, V1, P177
[10] ENOLBORATION .2. DICYCLOHEXYLCHLOROBORANE TRIETHYLAMINE AS A CONVENIENT REAGENT FOR REGIOSELECTIVE AND STEREOSELECTIVE ENOLBORATION OF REPRESENTATIVE CLASSES OF KETONES
BROWN, HC
DHAR, RK
GANESAN, K
SINGARAM, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) : 2716 - 2721

← 1 2 3 4 5 →