ENANTIOSELECTIVE CHIRAL BORANE-MEDIATED ALDOL REACTIONS OF SILYL KETENE ACETALS WITH ALDEHYDES - NOVEL EFFECT OF THE TRIALKYLSILYL GROUP OF THE SILYL KETENE ACETAL ON THE REACTION COURSE

被引：185

作者：

KIYOOKA, S

KANEKO, Y

KOMURA, M

MATSUO, H

NAKANO, M

机构：

[1] Department of Chemistry, Kochi University, Akebono-cho

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期

关键词：

D O I：

10.1021/jo00007a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioselective aldol reactions of silyl ketene acetals with a variety of aldehydes were achieved by using chiral boranes prepared from the sulfonamides of alpha-amino acids.

引用

页码：2276 / 2278

页数：3

共 9 条

[1]

Bosnich B., 1986, ASYMMETRIC CATALYSIS

[2] DRAMATIC CHANGES IN DIASTEREOSELECTIVITY WITH THE QUANTITY OF TITANIUM TETRACHLORIDE USED IN LEWIS ACID MEDIATED REACTIONS OF ALLYLSILANE WITH ALPHA-AMINO ALDEHYDES [J].

KIYOOKA, S ;

NAKANO, M ;

SHIOTA, F ;

FUJIYAMA, R .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5409-5411

[3] ASYMMETRIC ALDOL-TYPE REACTION BETWEEN BOTH ACHIRAL KETENE SILYL ACETALS AND ALDEHYDES BY THE USE OF A CHIRAL PROMOTER [J].

KOBAYASHI, S ;

SANO, T ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1989, (08) :1319-1322

[4] The identification of the amino acids - p-toluenesulfonyl - Chloride as a reagent [J].

McChesney, EW ;

Swann, WK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :1116-1118

[5]

NOYORI R, 1989, MODERN SYNTHETIC MET, V5, P116

[6]

REETZ MT, 1985, CHEM IND, P824

[7]

SARTOR D, 1990, SYNLETT, P197

[8]

TAKASU M, 1990, SYNLETT, P194

[9] ON 1,4-DIASTEREOSELECTIVITY IN THE ALDOL CONDENSATION OF METHYL KETONES [J].

TROST, BM ;

URABE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :3982-3983

← 1 →