ENANTIOSELECTIVE PROTONATION OF A SIMPLE ENOL - AMINOALCOHOL-CATALYZED KETONIZATION OF A PHOTOCHEMICALLY PRODUCED 2-METHYLINDEN-3-OL

被引：48

作者：

HENIN, F ^{[1
]}

MUZART, J ^{[1
]}

PETE, JP ^{[1
]}

MBOUNGOUMPASSI, A ^{[1
]}

RAU, H ^{[1
]}

机构：

[1] UNIV HOHENHEIM,FACHGEBIET PHYS CHEM,W-7000 STUTTGART 70,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 04期

关键词：

D O I：

10.1002/anie.199104161

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enol 2, produced by a Norrish type II photoelimination from 1, is protonated enantioselectively to ketone 3 in the presence of (-)-ephedrine. Best optical yields are obtained at 0-degrees-C using small amounts of the chiral aminoalcohol. There is still wide scope for optimization.

引用

页码：416 / 418

页数：3

共 42 条

[1] GENERATION OF SIMPLE ENOLS IN SOLUTION
CAPON, B
GUO, BZ
KWOK, FC
SIDDHANTA, AK
ZUCCO, C
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (04) : 135 - 140
[2] THE ENOL OF MANDELIC-ACID, DETECTION, ACIDITY IN AQUEOUS-SOLUTION, AND ESTIMATION OF THE KETO-ENOL EQUILIBRIUM-CONSTANT AND CARBON ACIDITY OF MANDELIC-ACID
CHIANG, Y
KRESGE, AJ
PRUSZYNSKI, P
SCHEPP, NP
WIRZ, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (07): : 792 - 794
[3] TEMPERATURE COEFFICIENTS OF THE RATES OF ACID-CATALYZED ENOLIZATION OF ACETONE AND KETONIZATION OF ITS ENOL IN AQUEOUS AND ACETONITRILE SOLUTIONS - COMPARISON OF THERMODYNAMIC PARAMETERS FOR THE KETO-ENOL EQUILIBRIUM IN SOLUTION WITH THOSE IN THE GAS-PHASE
CHIANG, Y
KRESGE, AJ
SCHEPP, NP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) : 3977 - 3980
[4] CHIANG Y, 1990, ANGEW CHEM, V102, P810
[5] ENANTIOSELECTIVITY IN ENEDIOL-HYDROXYKETONE TAUTOMERIZATION
DUHAMEL, L
LAUNAY, JC
[J]. TETRAHEDRON LETTERS, 1983, 24 (39) : 4209 - 4212
[6] LIGAND-EXCHANGE IN ASYMMETRIC REACTIONS OF LITHIUM ENOLATES - APPLICATION TO THE DERACEMIZATION OF ALPHA-AMINO-ACIDS
DUHAMEL, L
FOUQUAY, S
PLAQUEVENT, JC
[J]. TETRAHEDRON LETTERS, 1986, 27 (41) : 4975 - 4978
[7] ENANTIOSELECTIVE ELECTROPHILIC BOND CONSTRUCTION TO THE ALPHA-CARBON OF ALPHA-AMINOACIDS
DUHAMEL, L
DUHAMEL, P
FOUQUAY, S
EDDINE, J
PESCHARD, O
PLAQUEVENT, JC
RAVARD, A
SOLLIARD, R
VALNOT, JY
VINCENS, H
[J]. TETRAHEDRON, 1988, 44 (17) : 5495 - 5506
[8] DUHAMEL L, 1984, B SOC CHIM FR, V2, P421
[9] KINETICS OF THE ACETATE ION CATALYZED KETONIZATION OF 1,3-CYCLOHEXADIENOL - EQUILIBRIUM-CONSTANTS FOR THE ENOLIZATION OF 2-CYCLOHEXENONE AND 3-CYCLOHEXENONE
DZINGELESKI, GD
BLOTNY, G
POLLACK, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) : 1019 - 1023
[10] SYNTHESIS OF (R)-(+)-ALPHA-DAMASCONE AND (S)-(-)-ALPHA-DAMASCONE BY TANDEM GRIGNARD REACTION-ENANTIOSELECTIVE PROTONATION - EVIDENCE FOR THE INTERMEDIACY OF A CHIRAL COMPLEX
FEHR, C
GALINDO, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) : 6909 - 6911

← 1 2 3 4 5 →