KINETIC RESOLUTION OF RACEMIC ALLYLIC ACETATES BY ASYMMETRIC DIHYDROXYLATION (ADH) PROCESS - AN INDICATION OF PI-PI INTERACTION

被引：22

作者：

LOHRAY, BB

BHUSHAN, V

机构：

[1] Division of Organic Chemistry-Synthesis National Chemical Laboratory, Pune

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(00)79261-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Kinetic resolution of several racemic secondary allylic acetates have been examined using osmium tetroxide-cinchona alkaloid as chiral catalyst. The unexpected results have been rationalized with the help of model based on pi-pi interaction in the transition state apart from the matching and mismatching of the substrate and the catalyst.

引用

页码：3911 / 3914

页数：4

共 10 条

[1] PREPARATION OF CHIRAL COMPOUNDS WITH HIGH OPTICAL PURITY BY IRRADIATION WITH CIRCULARLY POLARIZED-LIGHT, A MODEL REACTION FOR PREBIOTIC GENERATION OF OPTICAL-ACTIVITY
BALAVOIN.G
MORADPOU.A
KAGAN, HB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (16) : 5152 - 5158
[2] KINETIC RESOLUTION STRATEGIES .1. ENHANCED PRODUCT ENANTIOMERIC EXCESSES AND YIELDS IN SHARPLESS EPOXIDATIONS
BROWN, SM
DAVIES, SG
DESOUSA, JAA
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (07) : 511 - 514
[3] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
GAO, Y
HANSON, RM
KLUNDER, JM
KO, SY
MASAMUNE, H
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
[4] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION
HAYASHI, T
YAMAMOTO, A
ITO, Y
NISHIOKA, E
MIURA, H
YANAGI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) : 6301 - 6311
[5] STEREOCHEMISTRY AND REGIOCHEMISTRY IN PALLADIUM-CATALYZED NUCLEOPHILIC-SUBSTITUTION OF OPTICALLY-ACTIVE (E)-ALLYL AND (Z)-ALLYL ACETATES
HAYASHI, T
YAMAMOTO, A
HAGIHARA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) : 723 - 727
[6] Kagan H. B., 1988, KINETIC RESOLUTION, V18, P249
[7] KITAMURA M, 1988, J ORG CHEM, V53, P710
[8] ON THE MECHANISM OF OSMIUM CATALYZED ASYMMETRIC DIHYDROXYLATION (ADH) OF ALKENES
LOHRAY, BB
BHUSHAN, V
[J]. TETRAHEDRON LETTERS, 1992, 33 (35) : 5113 - 5116
[9] RECENT ADVANCES IN THE ASYMMETRIC DIHYDROXYLATION OF ALKENES
LOHRAY, BB
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (11) : 1317 - 1349
[10] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT
SHARPLESS, KB
AMBERG, W
BENNANI, YL
CRISPINO, GA
HARTUNG, J
JEONG, KS
KWONG, HL
MORIKAWA, K
WANG, ZM
XU, DQ
ZHANG, XL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2768 - 2771

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