CHIRAL DIALKYL THIOPHOSPHORAMIDATES AS HIGHLY ENANTIOSELECTIVE CATALYSTS FOR THE ALKYLATION OF ALDEHYDES

被引：45

作者：

SOAI, K

HIROSE, Y

OHNO, Y

机构：

[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Shinjuku, Tokyo

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)80346-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral dialkyl thiophosphoramidates derived from norephedrine are highly enantioselective catalysts for the addition of dialkylzincs to aldehydes in the presence of titanium(IV) isopropoxide, and optically active sec -alcohols with up to 97% e.e. being obtained.

引用

页码：1473 / 1474

页数：2

共 14 条

[1] A NEW ROUTE TO N-MONOSUBSTITUTED THIOAMIDES UTILIZING PHOSPHORAMIDOTHIONATES AS REAGENTS FOR THE THIOAMIDATION OF CARBOXYLIC-ACIDS
DEBRUIN, KE
BOROS, EE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) : 6091 - 6098
[2] DESIGN AND REACTIVITY OF TOPOLOGICALLY UNIQUE, CHIRAL PHOSPHONAMIDES - REMARKABLE DIASTEREOFACIAL SELECTIVITY IN ASYMMETRIC OLEFINATION AND ALKYLATION
HANESSIAN, S
DELORME, D
BEAUDOIN, S
LEBLANC, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) : 5754 - 5756
[3] ITO K, 1992, SYNLETT, P573
[4] ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION
NOYORI, R
KITAMURA, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) : 49 - 69
[5] PREPARATION OF FUNCTIONALIZED DIALKYLZINC REAGENTS VIA AN IODINE ZINC EXCHANGE-REACTION - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF FUNCTIONALIZED SECONDARY ALCOHOLS
ROZEMA, MJ
SIDDURI, A
KNOCHEL, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) : 1956 - 1958
[6] CATALYTIC AND STOICHIOMETRIC ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES USING A NOVEL CHIRAL SPIROTITANATE
SCHMIDT, B
SEEBACH, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (01): : 99 - 101
[7] HIGHLY ENANTIOSELECTIVE ALKYLATION OF CARBON-NITROGEN DOUBLE-BONDS - CATALYTIC AND STOICHIOMETRIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE AMINES BY THE ENANTIOSELECTIVE ADDITION OF DIALKYLZINC REAGENTS TO N-DIPHENYLPHOSPHINOYLIMINES
SOAI, K
HATANAKA, T
MIYAZAWA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) : 1097 - 1098
[8] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES
SOAI, K
NIWA, S
[J]. CHEMICAL REVIEWS, 1992, 92 (05) : 833 - 856
[9] A NEW CHIRAL CATALYST FOR THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINC REAGENTS TO ALIPHATIC-ALDEHYDES
SOAI, K
YOKOYAMA, S
EBIHARA, K
HAYASAKA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (22) : 1690 - 1691
[10] STEREOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE SYN-1,3-DIOLS AND ANTI-1,3-DIOLS BY THE CATALYTIC ALKYLATION OF A BETA-ALKOXY ALDEHYDE
SOAI, K
HATANAKA, T
YAMASHITA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (13) : 927 - 929

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