DIASTEREOSELECTIVITY IN CONJUGATE ADDITION OF ALKYLCUPRATES TO VINYLOGOUS ESTER OF N,O-DIPROTECTED SERINAL

被引:35
作者
JAKO, I
UIBER, P
MANN, A
TADDEI, M
WERMUTH, CG
机构
[1] CNRS,CTR NEUROCHIM,DEPT PHARMACOCHIM MOLEC,5 RUE B PASCAL,F-67084 STRASBOURG,FRANCE
[2] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN U SCHIFF,I-50121 FLORENCE,ITALY
关键词
D O I
10.1016/S0040-4039(00)94416-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various alkylcuprates were added to the Z and E vinylogous esters of N,O-diprotected (D) or (L) serinal 1. Good to excellent yields and asymmetric inductions were observed. © 1990.
引用
收藏
页码:1011 / 1014
页数:4
相关论文
共 27 条
[1]   ORGANOCOPPER CONJUGATE ADDITION-REACTION IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].
ALEXAKIS, A ;
BERLAN, J ;
BESACE, Y .
TETRAHEDRON LETTERS, 1986, 27 (09) :1047-1050
[2]   ASYMMETRIC SYNTHESIS OF 3-ALKYLSUCCINALDEHYDIC ACID METHYL-ESTERS [J].
ASAMI, M ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1979, (05) :569-572
[3]   NOREPHEDRINE-DERIVED 2-ALKENYLOXAZOLIDINES - STEREOCHEMISTRY OF CYCLIZATION AND ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION [J].
BERNARDI, A ;
CARDANI, S ;
PILATI, T ;
POLI, G ;
SCOLASTICO, C ;
VILLA, R .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1600-1607
[4]   REGIOSPECIFIC ALKYLATION OF ENOLATE IONS IN LIQUID AMMONIA-TETRAHYDROFURAN [J].
BINKLEY, ES ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) :2156-2160
[5]   ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION OF CUPRATES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE - ENANTIOSELECTIVE SYNTHESIS OF 2-ALKYL-4-BENZYLOXYBUTANAL AND 2-ALKYL-4-OXOPENTANAL [J].
CARDANI, S ;
POLI, G ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON, 1988, 44 (18) :5929-5938
[6]  
COPPOLA GM, 1986, ASYMETRIC SYNTHESIS
[7]   EVIDENCE FOR A REVERSIBLE D,PI-STAR-COMPLEXATION, BETA-CUPRATION SEQUENCE IN THE CONJUGATE ADDITION-REACTION OF GILMAN REAGENTS WITH ALPHA-ENONES, BETA-ENONES [J].
COREY, EJ ;
BOAZ, NW .
TETRAHEDRON LETTERS, 1985, 26 (49) :6015-6018
[8]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[9]   STEREOSELECTIVE MONO-HOMOLOGATION AND BIS-HOMOLOGATION OF L-SERINAL VIA 2-TRIMETHYLSILYLTHIAZOLE ADDITION - THE THIAZOLE ROUTE TO AMINO L-SUGARS AND D-ERYTHRO-SPHINGOSINES [J].
DONDONI, A ;
FANTIN, G ;
FOGAGNOLO, M ;
MEDICI, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (01) :10-12