Highly regio- and enantioselective catalytic hydrogenation of enamides in conjugated diene systems:: Synthesis and application of γ,δ-unsaturated amino acids

被引：109

作者：

Burk, MJ ^{[1
]}

Allen, JG ^{[1
]}

Kiesman, WF ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Paul M Gross Chem Lab, Durham, NC 27708 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 04期

关键词：

D O I：

10.1021/ja9731074

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An extremely efficient method has been found for the catalytic asymmetric hydrogenation of conjugated alpha,gamma-dienamide esters using the Et-DuPHOS-Rh catalyst system. alpha,gamma-Dienamide ester substrates were prepared via the Suzuki cross-coupling reaction and the Horner-Emmons olefination. Full conversion to the corresponding gamma,delta-unsaturated amino acids with very high regio-and enantioselectivity was achieved after short reaction times. This new methodology was applied to the synthesis of the natural product bulgecinine from a prochiral dienamide ester.

引用

页码：657 / 663

页数：7

共 65 条

[1] ALLENE TRANSFER-REACTIONS - A NEW SYNTHESIS OF TERMINAL ALLENES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

BASAK, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1284-1285

[2] STEREOSELECTIVE SYNTHESIS OF THE DIHYDROXYISOLEUCINE CONSTITUENT OF THE AMANITA MUSHROOM TOXINS [J].

BARTLETT, PA ;

TANZELLA, DJ ;

BARSTOW, JF .

TETRAHEDRON LETTERS, 1982, 23 (06) :619-622

[3] BIOSYNTHESIS OF 2-AMINO-4-METHYLHEX-4-ENOIC ACID IN AESCULUS-CALIFORNICA - ROUTE FROM ISOLEUCINE AND ROLE OF AMINOTRANSFERASES [J].

BOYLE, JE ;

FOWDEN, L .

PHYTOCHEMISTRY, 1971, 10 (11) :2671-&

[4]

BOYLE JE, 1971, PHYTOCHEMISTRY, V10, P359

[5] CATECHOLBORANE (1,3,2-BENZODIOXABOROLE) AS A NEW, GENERAL MONOHYDROBORATION REAGENT FOR ALKYNES - CONVENIENT SYNTHESIS OF ALKENEBORONIC ESTERS AND ACIDS FROM ALKYNES VIA HYDROBORATION [J].

BROWN, HC ;

GUPTA, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) :4370-&

[6] THE MECHANISM OF ASYMMETRIC HYDROGENATION - CHIRAL BIS(DIPHENYLPHOSPHINO)-ALPHA-PHENYLALKANE COMPLEXES IN CATALYTIC AND STRUCTURAL STUDIES [J].

BROWN, JM ;

MURRER, BA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (04) :489-497

[7] STRUCTURAL CHARACTERIZATION OF A TRANSIENT INTERMEDIATE IN RHODIUM-CATALYZED ASYMMETRIC HOMOGENEOUS HYDROGENATION [J].

BROWN, JM ;

CHALONER, PA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (08) :344-346

[8] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

NUGENT, WA ;

HARLOW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138

[9] ASYMMETRIC CATALYTIC SYNTHESIS OF BETA-BRANCHED AMINO-ACIDS VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ ;

GROSS, MF ;

MARTINEZ, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) :9375-9376

[10] NEW CHIRAL 1,1'-BIS(PHOSPHOLANO)FERROCENE LIGANDS FOR ASYMMETRIC CATALYSIS [J].

BURK, MJ ;

GROSS, MF .

TETRAHEDRON LETTERS, 1994, 35 (50) :9363-9366

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