A NEW ROUTE TO THE SYNTHESIS OF AMINO-ACIDS THROUGH THE MERCURY CYCLIZATION OF CHIRAL AMIDALS

被引：30

作者：

AMOROSO, R ^{[1
]}

CARDILLO, G ^{[1
]}

TOMASINI, C ^{[1
]}

TORTORETO, P ^{[1
]}

机构：

[1] UNIV BOLOGNA,CTR STUDIO FIS MACROMOLEC,DIPARTIMENTO CHIM G CIAMICIAN,I-40126 BOLOGNA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 04期

关键词：

D O I：

10.1021/jo00030a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By means of the mercury cyclization of the unsaturated amidals 3a-e, obtained from the reaction of 1,3,5-tris-[(S)-phenylethyl]hexahydrotriazine (1) and alpha,beta-unsaturated acyl chlorides, diastereomeric mixtures of imidazolidin-4-ones 5-8 and perihydropyrimidin-4-ones 9-10 have been synthesized and easily separated by flash chromatography. The subsequent hydrolysis under acid conditions of the separated heterocycles affords respectively D or L alpha- and beta-amino acids. The regiochemistry of the cyclization has been studied, depending on the substituents of the double bond. Furthermore the absolute configuration of the newly introduced stereogenic center has been attributed on the basis of the H-1 NMR spectra of the heterocycles.

引用

页码：1082 / 1087

页数：6

共 31 条

[1]

ALLINGER NL, 1984, PROGRAM MM2OP QCPE

[2] SYNTHESIS OF L AND D ALPHA-AMINO-ACIDS FROM CHIRAL AMIDALS [J].

AMOROSO, R ;

CARDILLO, G ;

TOMASINI, C .

TETRAHEDRON LETTERS, 1990, 31 (44) :6413-6416

[3] 1,3-ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS VIA 2,5-TRANS DISUBSTITUTED IMIDAZOLIDIN-4-ONES [J].

AMOROSO, R ;

CARDILLO, G ;

TOMASINI, C .

TETRAHEDRON LETTERS, 1991, 32 (17) :1971-1974

[4]

BARTLETT P, 1984, ASYMMETRIC SYNTHESIS, V3

[5]

BARTLETT PA, 1980, TETRAHEDRON, V36, P2

[6] A NEW SYNTHESIS OF BOTH THE ENANTIOMERS OF 4-AMINO-3-HYDROXYBUTANOIC ACID (GABOB) AND MM2 CALCULATIONS FOR ROTAMERS OF THE INTERMEDIATE OXAZOLIDIN-2-ONES [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

TETRAHEDRON, 1987, 43 (19) :4377-4383

[7] SYNTHESIS OF AMINOALCOHOLS VIA PERIHYDRO-1,3-OXAZIN-2-ONES AND ABSOLUTE-CONFIGURATION ASSIGNMENT THROUGH MM2 CALCULATIONS [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

CHEMISTRY LETTERS, 1988, (01) :87-90

[8] SYNTHESIS OF CHIRAL 1,2-DIAMINES [J].

BRUNI, E ;

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

TETRAHEDRON LETTERS, 1989, 30 (13) :1679-1682

[9] AN EFFICIENT SYNTHESIS OF (R)-(+)-PROPRANOLOL AND (S)-(-)-PROPRANOLOL FROM RESOLVED 5-IODOMETHYLOXAZOLIDIN-2-ONES [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

TETRAHEDRON, 1987, 43 (11) :2505-2512

[10] FUNCTIONALIZATION OF UNSATURATED AMIDES - SYNTHESIS OF CHIRAL ALPHA-HYDROXY OR BETA-HYDROXY ACIDS [J].

CARDILLO, G ;

HASHEM, MA ;

TOMASINI, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05) :1487-1488

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