On the synthesis of (S)-alpha-methylaspartic acid by diastereoselective alkylation of a chiral 2-cyanopropanoate.

被引：18
作者：
Cativiela, C
DiazdeVillegas, MD
Galvez, JA
Lapena, Y
机构：
[1] Inst. De Cie. De Mat. De Aragon, Depto. De Quim. Orgánica, Universidad De Zaragoza-C.S.I.C
来源：
TETRAHEDRON | 1997年 / 53卷 / 16期
关键词：
D O I：
10.1016/S0040-4020(97)00249-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient procedure for the synthesis of optically pure alpha-methylaspartic acid, based on the diastereoselective alkylation of (1S,2R,4R)-10-(dicyclohexylsulfamoyl)iso 2-cyanopropanoate with alpha-halocarbonyl compounds, is described. (C) 1997 Elsevier Science Ltd.
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页码：5891 / 5898
页数：8
相关论文
共 38 条
[1]   RESOLUTION AND REGIOSELECTIVE PROTECTION OF GLUTAMIC-ACID ANALOGS .1. RESOLUTION OF DIASTEREOMERIC ALPHA-BOROXAZOLIDONE DERIVATIVES [J].
ACHER, F ;
AZERAD, R .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :731-744
[2]   OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ASPARTIC AND GLUTAMIC-ACID THROUGH DILITHIUM ENOLATOCARBOXYLATES OF 2-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]ACETIC AND 3-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]PROPIONIC ACID, RESPECTIVELY [J].
AEBI, JD ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1985, 68 (06) :1507-1518
[3]   VERSATILE STEREOSELECTIVE SYNTHESIS OF COMPLETELY PROTECTED TRIFUNCTIONAL ALPHA-METHYLATED ALPHA-AMINO-ACIDS STARTING FROM ALANINE [J].
ALTMANN, E ;
NEBEL, K ;
MUTTER, M .
HELVETICA CHIMICA ACTA, 1991, 74 (04) :800-806
[4]  
BADORREY R, 1997, TETRAHEDORN ASYMMETR, V8, P1
[5]   CONFORMATIONALLY RESTRICTED AMINO-ACIDS - DIASTEREOSELECTIVE SUBSTITUTION AT THE BETA-POSITION OF L-TRYPTOPHAN [J].
BRUNCKO, M ;
CRICH, D .
TETRAHEDRON LETTERS, 1992, 33 (42) :6251-6254
[6]  
CATIVIELA C, 1994, SYNLETT, P302
[7]   ASYMMETRIC-SYNTHESIS OF 3,3-DIPHENYL-2-METHYLALANINE, A NEW UNUSUAL ALPHA-AMINO-ACID FOR PEPTIDES OF BIOLOGICAL INTEREST [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON, 1994, 50 (32) :9837-9846
[8]   ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - HIGHLY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL 2-CYANO ESTERS [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2497-2505
[9]   SYNTHESIS OF (R)-2-AMINO-2-METHYLBUTANOIC ACID AND (S)-2-AMINO-2-METHYLBUTANOIC ACID (IVA) IN ENANTIOMERICALLY PURE FORM [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1445-1448
[10]   CHIRAL 2-CYANOCINNAMATES IN CONJUGATE ADDITION ASYMMETRIC ENOLATE TRAPPING REACTIONS [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (06) :1657-1661
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