SELF-REPRODUCTION OF CHIRALITY - ASYMMETRIC-SYNTHESIS OF BETA-ALKYL-BETA-AMINO ACIDS FROM ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES

被引:20
作者
CHU, KS [1 ]
KONOPELSKI, JP [1 ]
机构
[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064
关键词
D O I
10.1016/0040-4020(93)80005-E
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically pure heterocycle 2 is deprotonated at C6 with tert-butyllithium at -78-degrees-C. The resulting carbanion reacts with alkyl halides and aldehydes to give the corresponding alkylated products. Reduction of the double bond followed by hydrolysis affords enantiomerically pure beta-alkyl-beta amino acids.
引用
收藏
页码:9183 / 9190
页数:8
相关论文
共 45 条
[1]   HIGHLY DIASTEREOSELECTIVE ALKYLATION OF 6-METHYLPERIHYDROPYRIMIDIN-4-ONES DIRECTED TOWARDS THE SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACIDS [J].
AMOROSO, R ;
CARDILLO, G ;
TOMASINI, C .
TETRAHEDRON LETTERS, 1992, 33 (19) :2725-2728
[2]   HYDROGENATION OF BETA-AMINO-ALPHA,BETA-UNSATURATED ESTERS [J].
AUGUSTIN.RL ;
BELLINA, RF ;
GUSTAVSE.AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (03) :1287-+
[3]  
BALENOVIC K, 1952, J CHEM SOC, P3316
[4]  
BLASTICIDIN S, 1966, TETRAHEDRON LETT, P3785
[5]   ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES AS REAGENTS AND AUXILIARIES FOR ASYMMETRIC-SYNTHESIS [J].
CHU, KS ;
NEGRETE, GR ;
KONOPELSKI, JP ;
LAKNER, FJ ;
WOO, NT ;
OLMSTEAD, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1800-1812
[6]   ASYMMETRIC TOTAL SYNTHESIS OF (+)-JASPLAKINOLIDE [J].
CHU, KS ;
NEGRETE, GR ;
KONOPELSKI, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5196-5202
[7]   HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACID-ESTERS AND BETA-LACTAMS FROM ACHIRAL ESTERS AND IMINES [J].
COREY, EJ ;
DECICCO, CP ;
NEWBOLD, RC .
TETRAHEDRON LETTERS, 1991, 32 (39) :5287-5290
[8]   ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].
DAVIES, SG ;
ICHIHARA, O .
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :183-186
[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]   DIRECT, HIGHLY EFFICIENT SYNTHESIS FROM (S)-(+)-PHENYLGLYCINE OF THE TAXOL AND TAXOTERE SIDE-CHAINS [J].
DENIS, JN ;
CORREA, A ;
GREENE, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6939-6942