ASYMMETRIC-SYNTHESIS OF 3,3-DIPHENYL-2-METHYLALANINE, A NEW UNUSUAL ALPHA-AMINO-ACID FOR PEPTIDES OF BIOLOGICAL INTEREST

被引：31
作者：
CATIVIELA, C
DIAZDEVILLEGAS, MD
GALVEZ, JA
机构：
[1] Instituto de Ciencia de Materiales de Aragón, Departamento de Química Orgánica, Univesidad de Zaragoza-CSIC
来源：
TETRAHEDRON | 1994年 / 50卷 / 32期
关键词：
D O I：
10.1016/S0040-4020(01)85549-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A strategy of highly stereoselective enolate trapping of lithium (1S,1R,4R)-10-dicyclohexylsulfamoylisobornyl-2-cyano-3,3-diphenylpropanoate combined with the appropriate rearrangement process allows the asymmetric synthesis of a novel a-methyl amino acid derived from 3,3-diphenylalanine (Dip).
引用
收藏
页码：9837 / 9846
页数：10
相关论文
共 31 条
[1]   CONFORMATIONAL STUDIES ON PEPTIDES CONTAINING ENANTIOMERIC ALPHA-METHYL ALPHA-AMINO-ACIDS .1. DIFFERENTIAL CONFORMATIONAL PROPERTIES OF (R)-2-METHYLASPARTIC AND (S)-2-METHYLASPARTIC ACID [J].
ALTMANN, KH ;
ALTMANN, E ;
MUTTER, M .
HELVETICA CHIMICA ACTA, 1992, 75 (04) :1198-1210
[2]   CYCLIC-DERIVATIVES OF 3,3-DIPHENYLALANINE (DIP) (II), NOVEL ALPHA-AMINO-ACIDS FOR PEPTIDES OF BIOLOGICAL INTEREST [J].
BEYLIN, VG ;
CHEN, HG ;
DUNBAR, J ;
GOEL, OP ;
HARTER, W ;
MARLATT, M ;
TOPLISS, JG .
TETRAHEDRON LETTERS, 1993, 34 (06) :953-956
[3]   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
[4]   SYNTHESIS OF (R)-3-ALKYL-3-BENZYL-2-AZETIDINONES IN ENANTIOMERICALLY PURE FORM [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :229-238
[5]   NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-METHYLPHENYLALANINE [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :261-268
[6]  
CATIVIELA C, 1993, TETRAHEDRON-ASYMMETR, V4, P1145
[7]  
CATIVIELA C, 1994, J ORG CHEM, V54, P2497
[8]  
CATIVIELA C, 1993, SYNLETT, P302
[9]   CHIRAL SYNTHESIS OF D-3,3-DIPHENYLALANINE AND L-3,3-DIPHENYLALANINE (DIP), UNUSUAL ALPHA-AMINO-ACIDS FOR PEPTIDES OF BIOLOGICAL INTEREST [J].
CHEN, HG ;
BEYLIN, VG ;
MARLATT, M ;
LEJA, B ;
GOEL, OP .
TETRAHEDRON LETTERS, 1992, 33 (23) :3293-3296
[10]   CONFORMATIONALLY CONSTRAINED AMINO-ACIDS - SYNTHESIS AND OPTICAL RESOLUTION OF 3-SUBSTITUTED PROLINE DERIVATIVES [J].
CHUNG, JYL ;
WASICAK, JT ;
ARNOLD, WA ;
MAY, CS ;
NADZAN, AM ;
HOLLADAY, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :270-275
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