HIGHLY DIASTEREOSELECTIVE REDUCTION OF (-) MENTHYLPHENYLGLYOXALATE AND (-) MENTHYLPYRUVATE USING NEW HINDERED LITHIUMTRIALKOXYALUMINOHYDRIDES

被引：13

作者：

BOIREAU, G

DEBERLY, A

机构：

[1] Institut de Chimie Moléculaire d'Orsay Laboratoire de Chimie Organométallique, Université de Paris-Sud, Centre d'Orsay

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(00)80456-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reduction of the keto group of (-)menthylphenylglyoxalate and (-)menthyl pyruvate can be achieved with high diastereoisomeric excess (80-90%) using newly synthesized hindered lithium trialkoxyaluminium hydrides in THF at -78-degrees-C. Hindered borohydrides such as lithium trisiamylborohydride reduce those ketoesters with a lower diastereoselectivity.

引用

页码：771 / 774

页数：4

共 10 条

[1] SYNTHESIS OF OPTICALLY ACTIVE ALPHA-HYDROXY ACIDS BY ADDITION OF ORGANOZINE COMPOUNDS TO (-)MENTHYL PHENYLGLYOXALATE
BOIREAU, G
DEBERLY, A
ABENHAIM, D
[J]. TETRAHEDRON, 1989, 45 (18) : 5837 - 5844
[2] ENAMTIOMERIC PURITY OF PHENYLETHYLENE GLYCOLE AND RELIABILITY OF PHENYLGLYOXYLATE ASYMMETRIC REDUCTIONS IN CONFIGURATIONAL ASSIGNMENTS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) : 4002 - &
[3] DEBERLY A, 1984, TETRAHEDRON LETT, P655
[4] HOREAU A, 1968, B SOC CHIM FR, P3795
[5] KIRSHNAMURTHY S, 1976, J AM CHEM SOC, P3383
[6] LITHIUM "TRIS[(3-ETHYL-3-PENTYL)OXY]ALUMINUM HYDRIDE - A NEW REMARKABLY CHEMOSELECTIVE REAGENT FOR THE REDUCTION OF ALDEHYDES IN THE PRESENCE OF KETONES
KRISHNAMURTHY, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) : 4628 - 4629
[7] MORISSON JD, 1971, ASYMMETRIC ORGANIC R, P50
[8] UNTERSUCHUNGEN UBER ASYMMETRISCHE SYNTHESEN .5. UBER DEN STERISCHEN VERLAUF DER REDUKTION VON ALPHA-KETOSAURE-ESTERN OPTISCH AKTIVER ALKOHOLE MIT LITHIUMALUMINIUMHYDRID
PRELOG, V
WILHELM, M
BRIGHT, DB
[J]. HELVETICA CHIMICA ACTA, 1954, 37 (01) : 221 - 224
[9] ASYMMETRIC INDUCTION - REDUCTION, NUCLEOPHILIC-ADDITION TO, AND ENE REACTIONS OF CHIRAL ALPHA-KETOESTERS
WHITESELL, JK
DEYO, D
BHATTACHARYA, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (15) : 802 - 802
[10] NEW PERSPECTIVES IN ASYMMETRIC INDUCTION
WHITESELL, JK
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (09) : 280 - 284

← 1 →