Stereoselective synthesis of alpha-hydroxy-beta-amino acids using D-glyceraldehyde as the homochiral source.

被引:45
作者
Cativiela, C
DiazDeVillegas, MD
Galvez, JA
机构
[1] Inst. de Cie. de Mat. de Aragon, Depto. de Quim. Orgánica, Universidad de Zaragoza-C.S.I.C.
关键词
D O I
10.1016/0957-4166(96)00037-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.
引用
收藏
页码:529 / 536
页数:8
相关论文
共 45 条
[1]   SYNTHESIS AND ANTIHERPETIC ACTIVITY OF (S)-9-[2,3-DIHYDROXY-1-PROPOXY)METHYL]GUANINE, (R)-9-[2,3-DIHYDROXY-1-PROPOXY)METHYL]GUANINE, AND (+/-)-9-[(2,3-DIHYDROXY-1-PROPOXY)METHYL]GUANINE, LINEAR ISOMERS OF 2'-NOR-2'-DEOXYGUANOSINE [J].
ASHTON, WT ;
CANNING, LF ;
REYNOLDS, GF ;
TOLMAN, RL ;
KARKAS, JD ;
LIOU, R ;
DAVIES, MEM ;
DEWITT, CM ;
PERRY, HC ;
FIELD, AK .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (07) :926-933
[2]   A CHEMOENZYMATIC APPROACH TO CHIRAL PHENYLISOSERINATES USING 4-ISOPROPYL-2-OXAZOLIN-5-ONE AS MASKED UMPOLED SYNTHON FOR HYDROXYCARBONYL ANION [J].
BARCO, A ;
BENETTI, S ;
DERISI, C ;
POLLINI, GP ;
ROMAGNOLI, R ;
ZANIRATO, V .
TETRAHEDRON LETTERS, 1994, 35 (49) :9289-9292
[3]   A NEW ALPHA-SELECTIVE SYNTHETIC EQUIVALENT FOR THE CROTYL ANION IN ADDITIONS TO IMINES [J].
BETZ, J ;
HEUSCHMANN, M .
TETRAHEDRON LETTERS, 1995, 36 (23) :4043-4046
[4]  
BOINI C, 1994, J CHEM SOC CHEM COMM, P2767
[5]   A PRACTICAL ACCESS TO CHIRAL PHENYLISOSERINATES, PREPARATION OF TAXOTERE(R) ANALOGS [J].
BOURZAT, JD ;
COMMERCON, A .
TETRAHEDRON LETTERS, 1993, 34 (38) :6049-6052
[6]   ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID [J].
BUNNAGE, ME ;
BURKE, AJ ;
DAVIES, SG ;
GOODWIN, CJ .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :165-176
[7]   DIASTEREOSELECTIVE STRECKER REACTION OF IMINES DERIVED FROM D-GLYCERALDEHYDE - A NEW ROUTE TO BETA-HYDROXY-ALPHA-AMINO ACIDS [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON LETTERS, 1995, 36 (16) :2859-2860
[8]   IMPROVED PROTECTION AND ESTERIFICATION OF A PRECURSOR OF THE TAXOTERE(R) AND TAXOL SIDE-CHAINS [J].
COMMERCON, A ;
BEZARD, D ;
BERNARD, F ;
BOURZAT, JD .
TETRAHEDRON LETTERS, 1992, 33 (36) :5185-5188
[9]   ASYMMETRIC-SYNTHESIS OF SULFINIMINES - APPLICATIONS TO THE SYNTHESIS OF NONRACEMIC BETA-AMINO-ACIDS AND ALPHA-HYDROXYL-BETA-AMINO-ACIDS [J].
DAVIS, FA ;
REDDY, RT ;
REDDY, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6387-6389
[10]   A PRACTICAL, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN VIA ASYMMETRIC CATALYSIS [J].
DENG, L ;
JACOBSEN, EN .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4320-4323