ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES BY ALKYLATION OF CHIRAL PHOSPHONOGLYCINE EQUIVALENTS - ROLE OF CHELATING EFFECTS

被引：14

作者：

JOMMI, G

MIGLIERINI, G

PAGLIARIN, R

SELLO, G

SISTI, M

机构：

[1] Universitá degli Studi, Milano - Dipartimento di Chimica Organica e Industriale -, 20133 Milano, via G. Venezian

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(00)82094-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diethyl alpha-amino-alpha-alkyl-phosphonates are obtained in good to high enantiomeric excesses by alkylation of chiral phosphonoglycine equivalents embodying the camphor skeleton. The chelating effects in the alkylation step play an important role in enhancing the diastereoselectivity of the reaction as substantiated by semiempirical calculations (AM1).

引用

页码：1131 / 1134

页数：4

共 14 条

[1] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].

ALLEN, MC ;

FUHRER, W ;

TUCK, B ;

WADE, R ;

WOOD, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661

[2]

BENMARK SE, 1992, TETRAHEDRON, V48, P2191

[3] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[4] OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].

DHAWAN, B ;

REDMORE, D .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144

[5] ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES BY ALKYLATION OF THE CHIRAL SCHIFF-BASE DERIVED FROM (+)-KETOPINIC ACID AND DIETHYLAMINOMETHYL PHOSPHONATE [J].

FERRARI, M ;

JOMMI, G ;

MIGLIERINI, G ;

PAGLIARIN, R ;

SISTI, M .

SYNTHETIC COMMUNICATIONS, 1992, 22 (01) :107-123

[6] PHOSPHORUS AMINO-ACID-ANALOGS AS INHIBITORS OF LEUCINE AMINOPEPTIDASE [J].

GIANNOUSIS, PP ;

BARTLETT, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) :1603-1609

[7] ASYMMETRIC SYNTHESIS OF ALPHA AMINOPHOSPHONIC ACIDS .4. ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE PHOSPHONIC ANALOGS OF GLUTAMIC-ACID AND PROLINE [J].

GROTH, U ;

RICHTER, L ;

SCHOLLKOPF, U .

TETRAHEDRON, 1992, 48 (01) :117-122

[8] SYNTHESIS OF (1R) -[1-D]-ALPHA-FENCHOCAMPHORONEQUINONE [J].

KOKKE, WCMC ;

VARKEVIS.FA .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1653-1656

[9]

LASCHAT S, 1992, SYNTHESIS-STUTTGART, P90

[10] SYNTHESIS OF ALPHA-ALKYL-SUBSTITUTED AND GAMMA-ALKYL-SUBSTITUTED PHOSPHINOTHRICINS - POTENT NEW INHIBITORS OF GLUTAMINE-SYNTHETASE [J].

LOGUSCH, EW ;

WALKER, DM ;

MCDONALD, JF ;

LEO, GC ;

FRANZ, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4069-4074

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