Enantioselective synthesis of 2-allyl and 2-(3-trimethyl-silylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation

被引：8

作者：

Devaux, JM ^{[1
]}

Goré, J ^{[1
]}

Vatèle, JM ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, Lab Chim Organ 1, CPE, F-69622 Villeurbanne, France

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(98)00144-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1619 / 1626

页数：8

共 50 条

[1] Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2;: Dual role of the cinchona alkaloid ligand
Jonsson, SY
Adolfsson, H
Bäckvall, JE
ORGANIC LETTERS, 2001, 3 (22) : 3463 - 3466
[2] PRECLUSION OF THE 2ND CYCLE IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS LEADS TO A SUPERIOR PROCESS
KWONG, HL
SORATO, C
OGINO, Y
HOU, C
SHARPLESS, KB
TETRAHEDRON LETTERS, 1990, 31 (21) : 2999 - 3002
[3] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF CIS-FUSED CYCLOPENTENO-1,2,4-TRIOXANES
JEFFORD, CW
MISRA, D
DISHINGTON, AP
TIMARI, G
ROSSIER, JC
BERNARDINELLI, G
TETRAHEDRON LETTERS, 1994, 35 (34) : 6275 - 6278
[4] Density functional study of the [2+2]- and [2+3]-cycloaddition mechanisms for the osmium-catalyzed dihydroxylation of olefins
Torrent, M
Deng, LQ
Duran, M
Sola, M
Ziegler, T
ORGANOMETALLICS, 1997, 16 (01) : 13 - 19
[5] Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2 using a biomimetic flavin-based coupled catalytic system
Jonsson, SY
Färnegårdh, K
Bäckvall, JE
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (07) : 1365 - 1371
[6] TOWARD AN UNDERSTANDING OF THE HIGH ENANTIOSELECTIVITY IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION .2. A QUALITATIVE MOLECULAR MECHANICS APPROACH
NORRBY, PO
KOLB, HC
SHARPLESS, KB
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8470 - 8478
[7] Clean osmium-catalyzed asymmetric dihydroxylation of olefins in ionic liquids and supercritical CO2 product recovery
Branco, LC
Serbanovic, A
da Ponte, MN
Afonso, CAM
CHEMICAL COMMUNICATIONS, 2005, (01) : 107 - 109
[8] A NEW PROCEDURE FOR CONSTRUCTION OF 2,6-TRANS-DISUBSTITUTED PIPERIDINES USING OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - APPLICATION TO THE SYNTHESIS OF (+)-EPIDIHYDROPINIDINE AND (+)-SOLENOPSIN-A
TAKAHATA, H
INOSE, K
ARAYA, N
MOMOSE, T
HETEROCYCLES, 1994, 38 (09) : 1961 - 1964
[9] Combining Q2MM modeling and kinetic studies for refinement of the osmium-catalyzed asymmetric dihydroxylation (AD) mnemonic
Fristrup, Peter
Jensen, Gitte Holm
Andersen, Marie Louise Nygaard
Tanner, David
Norrby, Per-Ola
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (10) : 2182 - 2198
[10] Updating the asymmetric osmium-catalyzed dihydroxylation (AD) mnemonic: Q2MM modeling and new kinetic measurements
Fristrup, P
Tanner, D
Norrby, PO
CHIRALITY, 2003, 15 (04) : 360 - 368

← 1 2 3 4 5 →