Refined enantioselective methylation catalysts: improved routes to bifunctional C5 synthons

被引：39

作者：

Jones, GB ^{[1
]}

Guzel, M ^{[1
]}

Chapman, BJ ^{[1
]}

机构：

[1] Clemson Univ, Dept Chem, Med Chem Lab, Clemson, SC 29634 USA

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(98)00076-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Catalytic enantioselective routes to bifunctional C5 synthons, including those of the macrolide (S)-(-)-zearalenone have been achieved. Stereochemistry was introduced using a mixed ligand arene chromium tricarbonyl catalyst to mediate the enantioselective addition of dimethyl zinc to a functionalized aldehyde. Comparison with alternate reduction strategies is presented. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：901 / 905

页数：5

共 20 条

[1] ASYMMETRIC BORANE REDUCTION OF ACHIRAL KETONES MEDIATED BY A-CHIRAL OXAZABOROLIDINE DERIVED FROM (-)-EPHEDRINE [J].

CHO, BT ;

CHUN, YS .

TETRAHEDRON-ASYMMETRY, 1992, 3 (12) :1539-1542

[2] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[3]

DISIMONE B, 1995, TETRAHEDRON-ASYMMETR, V6, P301

[4]

Hanessian S., 1983, Total Synthesis of Natural Products: The Chiron Approach

[5] CHIRAL ARENE CHROMIUM TRICARBONYL COMPLEXES AS ENANTIOSELECTIVE CATALYSTS - HIGHLY SELECTIVE 1,2 ALKYL ADDITIONS TO ALDEHYDES [J].

HEATON, SB ;

JONES, GB .

TETRAHEDRON LETTERS, 1992, 33 (13) :1693-1696

[6] SYNTHESIS OF MACROCYCLES VIA ALLYLIC RADICAL INTERMEDIATES - A TOTAL SYNTHESIS OF (-)-ZEARALENONE [J].

HITCHCOCK, SA ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1990, 31 (25) :3641-3644

[7]

JONES GB, 1993, SYNLETT, P367

[8] Catalytic enantioselective synthesis of macrolides via asymmetric alkylation [J].

Jones, GB ;

Huber, RS ;

Chapman, BJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1797-1809

[9] CATALYTIC ENANTIOSELECTIVE MACROLIDE SYNTHESIS .2. USE OF DIFFERENTIAL DEPROTECTION PROTOCOLS [J].

JONES, GB ;

CHAPMAN, BJ ;

HUBER, RS ;

BEATY, R .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1199-1202

[10] CATALYTIC ASYMMETRIC INDUCTION .2. CHIRAL TRICARBONYL (ETA-6 ARENE) CHROMIUM (0) COMPLEXES AS ENANTIOSELECTIVE CATALYSTS [J].

JONES, GB ;

HEATON, SB .

TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :261-272

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