ASYMMETRIC INTRAMOLECULAR HYDROSILYLATION OF HYDROXYKETONES

被引：34

作者：

BURK, MJ

FEASTER, JE

机构：

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 16期

关键词：

D O I：

10.1016/0040-4039(92)88150-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A procedure for the catalytic asymmetric intramolecular hydrosilylation of alpha- and beta-hydroxyketones has been developed. A cationic rhodium (I) catalyst bearing the new chiral diphosphine (R,R)-i-Pr-DuPHOS affords the product diols in up to 93% ee.

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页码：2099 / 2102

页数：4

相关论文

共 12 条

[1] 1,3-ASYMMETRIC VERSUS 1,2-ASYMMETRIC INDUCTION IN THE REDUCTION OF BETA-HYDROXY KETONES BY INTRAMOLECULAR HYDROSILYLATION [J].

ANWAR, S ;

BRADLEY, G ;

DAVIS, AP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1383-1389

[2] INTRAMOLECULAR HYDROSILYLATIONS .2. THE ANTI-SELECTIVE REDUCTION OF BETA-HYDROXYKETONES [J].

ANWAR, S ;

DAVIS, AP .

TETRAHEDRON, 1988, 44 (13) :3761-3770

[3] C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519

[4] ASYMMETRIC SYNTHESIS - PRODUCTION OF OPTICALLY-ACTIVE AMINO-ACIDS BY CATALYTIC-HYDROGENATION [J].

FRYZUK, MD ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (19) :6262-6267

[5]

HALPERN J, 1985, ASYMMETRIC SYNTHESIS, V5, pCH2

[6] ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].

JACOBSEN, EN ;

MARKO, I ;

MUNGALL, WS ;

SCHRODER, G ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970

[7] SILYLATIONS WITH BIS(TRIMETHYLSILYL)ACETAMIDE A HIGHLY REACTIVE SILYL DONOR [J].

KLEBE, JF ;

FINKBEIN.H ;

WHITE, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3390-&

[8]

KOENIG KE, 1985, ASYMMETRIC SYNTHESIS, V5, pCH3

[9] BINAP - AN EFFICIENT CHIRAL ELEMENT FOR ASYMMETRIC CATALYSIS [J].

NOYORI, R ;

TAKAYA, H .

ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (10) :345-350

[10] A LIGAND STRUCTURE-ENANTIOSELECTIVITY RELATIONSHIP FOR THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

OGINO, Y ;

CHEN, H ;

MANOURY, E ;

SHIBATA, T ;

BELLER, M ;

LUBBEN, D ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1991, 32 (41) :5761-5764