NEW CHIRAL AUXILIARIES - THEIR USE IN THE ASYMMETRIC HYDROGENATION OF BETA-ACETAMIDOCROTONATES

被引：80

作者：

POTIN, D ^{[1
]}

DUMAS, F ^{[1
]}

DANGELO, J ^{[1
]}

机构：

[1] ECOLE SUPER PHYS & CHIM IND VILLE PARIS,CNRS,UNITE CHIM ORGAN,10 RUE VAUQUELIN,F-75231 PARIS 05,FRANCE

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 09期

关键词：

D O I：

10.1021/ja00165a036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of chiral β-amido esters 7 with high diastereoisomeric excess was achieved by asymmetric hydrogenation (H2/PtO2) of stereogenic β-acetamidocrotonates 6 in which the chirality is present in the alkyl of the ester part. For such a purpose, new efficient chiral auxiliaries such as 2,2-diphenylcyclopentanol (12) and 1,1-diphenyl-3-methyl-2-butanol (13) were developed. © 1990, American Chemical Society. All rights reserved.

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页码：3483 / 3486

页数：4

相关论文

共 24 条

[1]

ACHINAMI K, 1979, Patent No. 119414

[2]

ACHIWA K, 1978, TETRAHEDRON LETT, P1119

[3] 2-ARYL-3-ACETYL-4(1H)-QUINOLONES [J].

ANDERSON, PC ;

STASKUN, B .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09) :3033-&

[4] HYDROBORATION .80. PREPARATION OF (TRANS-2-PHENYLCYCLOPENTYL)BORONATES AND (TRANS-2-PHENYLCYCLOHEXYL)BORONATES OF VERY HIGH ENANTIOMERIC PURITIES [J].

BROWN, HC ;

PRASAD, JVNV ;

GUPTA, AK ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :310-311

[5] CHIRAL SYNTHESIS VIA ORGANOBORANES .14. SELECTIVE REDUCTIONS .41. DIISOPINOCAMPHEYLCHLOROBORANE, AN EXCEPTIONALLY EFFICIENT CHIRAL REDUCING AGENT [J].

BROWN, HC ;

CHANDRASEKHARAN, J ;

RAMACHANDRAN, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1539-1546

[6]

BUSCHMANN H, 1988, SYNTHESIS-STUTTGART, P827

[7] DIKETENE [J].

CLEMENS, RJ .

CHEMICAL REVIEWS, 1986, 86 (02) :241-318

[8] PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION [J].

COREY, EJ ;

ENSLEY, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6908-6909

[9] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[10] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ESTERS THROUGH HIGH-PRESSURE-INDUCED ADDITION OF AMINES TO ALPHA,BETA-ETHYLENIC ESTERS [J].

DANGELO, J ;

MADDALUNO, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8112-8114