ACYCLIC STEREOCONTROL WITH O-PROTECTED 2S-HYDROXY-PROPANAL - SOLVENT EFFECT

被引:21
作者
CAINELLI, G
GIACOMINI, D
PERCIACCANTE, F
TRERE, A
机构
[1] Dipartimento di Chimica G.Ciamician Università di Bologna, I-40126 Bologna
关键词
D O I
10.1016/S0957-4166(00)86265-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The dependence of diastereofacial selectivity on the nature of ether solvents in addition reactions of homochiral O-protected lactic aldehyde with organomagnesium reagents is reported.
引用
收藏
页码:1913 / 1916
页数:4
相关论文
共 15 条
[1]   REVERSAL OF DIASTEREOSELECTIVITY IN THE ADDITION OF C-NUCLEOPHILES TO N-TRIMETHYLSILYL IMINES VIA GRIGNARD DERIVED ORGANO COPPER-BORON TRIFLUORIDE REAGENTS [J].
CAINELLI, G ;
GIACOMINI, D ;
PANUNZIO, M ;
ZARANTONELLO, P .
TETRAHEDRON LETTERS, 1992, 33 (50) :7783-7786
[2]   PREPARATION OF 1,2 AMINOLS FROM CYANOHYDRINS VIA N-DIISOBUTYLALUMINIUM IMINES [J].
CAINELLI, G ;
PANUNZIO, M ;
CONTENTO, M ;
GIACOMINI, D ;
MEZZINA, E ;
GIOVAGNOLI, D .
TETRAHEDRON, 1993, 49 (18) :3809-3826
[3]  
CAINELLI G, 1991, TETRAHEDRON LETT, V32, P2667
[4]   CHELATES AS INTERMEDIATES IN NUCLEOPHILIC ADDITIONS TO ALKOXY KETONES ACCORDING TO CRAM RULE (CYCLIC MODEL) [J].
CHEN, XN ;
HORTELANO, ER ;
ELIEL, EL ;
FRYE, SV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1778-1784
[5]   STUDIES IN STEREOCHEMISTRY .30. MODELS FOR STERIC CONTROL OF ASYMMETRIC INDUCTION [J].
CRAM, DJ ;
KOPECKY, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (11) :2748-2755
[6]   BASICITY OF SOLVENTS OF ORGANOMAGNESIUM COMPOUNDS [J].
DUCOM, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 59 (OCT1) :83-96
[7]   ASYMMETRIC-SYNTHESIS AND CRAMS (CHELATE) RULE [J].
ELIEL, EL ;
FRYE, SV ;
HORTELANO, ER ;
CHEN, XN ;
XU, B .
PURE AND APPLIED CHEMISTRY, 1991, 63 (11) :1591-1598
[8]   SIGNIFICANCE OF HALIDE IN GRIGNARD REAGENTS [J].
FRENCH, W ;
WRIGHT, GF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1964, 42 (11) :2474-&
[9]   H-1-NMR SPECTRA AND CONFORMATIONS OF PROPANE-1,2-DIOL, MESO-RACEMIC AND RACEMIC BUTANE-2,3-DIOLS, AND SOME ALDITOLS IN NONAQUEOUS MEDIA [J].
GALLWEY, FB ;
HAWKES, JE ;
HAYCOCK, P ;
LEWIS, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (11) :1979-1985
[10]   CHEMISTRY OF CARBANIONS .14. FACTORS INFLUENCING RATE OF ADDITION OF DIMETHYLMAGNESIUM TO BENZOPHENONE [J].
HOUSE, HO ;
OLIVER, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (03) :929-&