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

被引：58

作者：

GROTH, U ^{[1
]}

RICHTER, L ^{[1
]}

SCHOLLKOPF, U ^{[1
]}

机构：

[1] UNIV GOTTINGEN,INST ORGAN CHEM,TAMMANNSTR 2,W-3400 GOTTINGEN,GERMANY

来源：

TETRAHEDRON | 1992年 / 48卷 / 01期

关键词：

D O I：

10.1016/S0040-4020(01)80584-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition of the metallated camphor derivatives 2 to vinylogous esters and subsequential hydrolysis afforded phosphonic analogues of glutamic acid. The enantiomerically pure lactam 6 was reduced by LiBH4/BF3.OEt2 to phosphoproline 7.

引用

页码：117 / 122

页数：6

共 20 条

[1] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[2] OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS
DHAWAN, B
REDMORE, D
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4): : 119 - 144
[3] GRUSZECKA E, 1979, POL J CHEM, V53, P75
[4] A VERSATILE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO ALPHA-ALKYL-PHOSPHONIC ACIDS OF HIGH ENANTIOMERIC PURITY
HANESSIAN, S
BENNANI, YL
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6465 - 6468
[5] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS .2. ASYMMETRIC ADDITION OF A CHIRAL CYCLIC PHOSPHITE TO A CYCLIC IMINE - SYNTHESIS OF PHOSPHONIC ACID ANALOGS OF D-PENICILLAMINE AND L-PENICILLAMINE
HOPPE, I
SCHOLLKOPF, U
NIEGER, M
EGERT, E
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (12): : 1067 - 1068
[6] HOPPE I, 1985, ANGEW CHEM, V97, P1066
[7] NUCLEOPHILIC ADDITIONS TO N-GLYCOSYLNITRONES .4. ASYMMETRIC-SYNTHESIS OF N-HYDROXY-ALPHA-AMINOPHOSPHONIC AND ALPHA-AMINOPHOSPHONIC ACIDS
HUBER, R
VASELLA, A
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (06) : 1461 - 1476
[8] A PHOSPHONAMIDATE DIPEPTIDE ANALOG AS AN INHIBITOR OF CARBOXYPEPTIDASE-A
JACOBSEN, NE
BARTLETT, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) : 654 - 657
[9] SYNTHESIS OF ENANTIOMERICALLY PURE AMINOPHOSPHONIC ACIDS
JACQUIER, R
OUAZZANI, F
ROUMESTANT, ML
VIALLEFONT, P
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1988, 36 (1-2): : 73 - 77
[10] ISOMERIZATION OF ALKYL PHOSPHITES .7. SOME DERIVATIVES OF 2-BROMOETHANE PHOSPHONIC ACID
KOSOLAPOFF, GM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (05) : 1971 - 1972

← 1 2 →