(+/-)-3-METHYL-1,1-DIPHENYL-2-BUTYL 3-ACETAMIDOCROTONATE AND ITS HYDROGENATION PRODUCT

被引：2

作者：

CHIARONI, A ^{[1
]}

RICHE, C ^{[1
]}

DUMAS, F ^{[1
]}

POTIN, D ^{[1
]}

DANGELO, J ^{[1
]}

机构：

[1] CTR ETUD PHARMACEUT,BIOCIS,CNRS,UNITE RECH,F-92296 CHATENAY MALABRY,FRANCE

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS | 1995年 / 51卷

关键词：

D O I：

10.1107/S0108270193007383

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of (+/-)-3-methyl-1,1-diphenyl-2-butyl beta-acetamidobutanoate, C23H29NO3, (10), With high diastereoisomeric excess was achieved by asymmetric hydrogenation of the stereogenic title compound, C23H27NO3, (9), in which the chirality is present in the ester part. The acetamidocrotonate (9) is planar and delimits a pro-R and a pro-S face. An intramolecular hydrogen bond between the amino group and the carboxylate group is essential to ensure planarity. One of the phenyl rings of the ester hinders one face. The hydrogenation occurs by the opposite face as proved by the crystal structure of its product of hydrogenation, (10).

引用

页码：967 / 970

页数：4

共 9 条

[1] 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

[2] SEMIEMPIRICAL CALCULATIONS OF THE DISPERSION CONTRIBUTION TO THE PROTON CHEMICAL-SHIFT [J].

GIESSNERPRETTRE, C ;

GRESH, N ;

MADDALUNO, J .

JOURNAL OF MAGNETIC RESONANCE, 1992, 99 (03) :605-610

[3]

JOHNSON CK, 1965, ORNL3794 REP

[4]

POTIN D, 1990, J AM CHEM SOC, V112, P3484

[5]

RICHE C, 1983, R3M REPRESENTATION M

[6]

RICHE C, 1989, NONIUS PROGRAM DATA

[7]

RICHE C, 1992, ACTACIF

[8]

Sheldrick G. M., 1985, SHELXS86 PROGRAM SOL

[9]

SHELDRICK GM, 1976, SHELX PROGRAM CRYSTA

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