Highly stereoselective indium trichloride-catalysed asymmetric aldol reaction of formaldehyde and a glucose-derived silyl enol ether in water

被引：43

作者：

Loh, TP ^{[1
]}

Chua, GL ^{[1
]}

Vittal, JJ ^{[1
]}

Wong, MW ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 08期

关键词：

D O I：

10.1039/a800486b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The yield and stereochemical outcome of the reaction between D-glucose-derived silyl enol ether 1 (Z and E isomers) and commercial formaldehyde in water catalysed by indium(III) choride was studied.

引用

页码：861 / 862

页数：2

共 8 条

[1] Dondoni A., 1997, PREPARATIVE CARBOHYD, P173
[2] EVANS DA, 1984, ASYMMETRIC SYNTHES B, V3, P12
[3] FRISCH MJ, 1992, GAUSSIAN 92 DFT
[4] SPECIFIC ENOLATES FROM ALPHA-AMINO KETONES
GARST, ME
BONFIGLIO, JN
GRUDOSKI, DA
MARKS, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12) : 2307 - 2315
[5] Hehre W.J., 1986, AB INITIO MOL THEORY
[6] LANTHANIDE TRIFLATES AS WATER-TOLERANT LEWIS-ACIDS - ACTIVATION OF COMMERCIAL FORMALDEHYDE SOLUTION AND USE IN THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA
KOBAYASHI, S
HACHIYA, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) : 3590 - 3596
[7] ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION
LI, CJ
[J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2023 - 2035
[8] Indium trichloride catalysed Mukaiyama aldol reaction in water
Loh, TP
Pei, JA
Cao, GQ
[J]. CHEMICAL COMMUNICATIONS, 1996, (15) : 1819 - 1820

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