(S,S)-BIS-PARA-TOLYLSULFINYLMETHANE AND CARBONYL-COMPOUNDS - REACTIVITY AND ASYMMETRIC INDUCTION

被引:28
作者
SOLLADIE, G [1 ]
COLOBERT, F [1 ]
RUIZ, P [1 ]
HAMDOUCHI, C [1 ]
CARRENO, MC [1 ]
RUANO, JLG [1 ]
机构
[1] UNIV AUTONOMA MADRID,DEPT QUIM,E-28049 MADRID,SPAIN
关键词
ASYMMETRIC SYNTHESIS; CHIRAL SULFOXIDES; (S; S)-BIS-P-TOLYLSULFINYLMETHANE; 4-SUBSTITUTED (E,E)-(S,S)-1,1-BIS-(PARA-TOLYL-SULFINYL)-1,3-BUTADIENES;
D O I
10.1016/S0040-4039(00)79770-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(S,S)-bis p-Tolylsulfinylmethane was shown to react with aromatic aldehydes with a high diastereoselectivity. In contrast, ,beta-unsaturated aldehydes, giving only the elimination products, are in one step transformed into 4-substituted (E,E)-(S,S)-1,1-bis (p-tolylsulfinyl)-1,3-butadiene.
引用
收藏
页码:3695 / 3698
页数:4
相关论文
共 10 条
[1]   SYNTHESIS AND STEREOMUTATION OF OPTICALLY-ACTIVE ALPHA-CYANOSULFOXIDES [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COLONNA, S ;
COZZI, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :614-617
[2]   DIASTEREOSELECTIVE ADDITION OF (R)-METHYL PARA-TOLYL SULFOXIDE TO BENZALDEHYDE [J].
BRAUN, M ;
HILD, W .
CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (01) :413-414
[3]   CHIRAL ACYL ANION AND ENOLONIUM ION EQUIVALENTS - ASYMMETRIC-SYNTHESIS OF ALPHA-METHOXY-ALDEHYDES [J].
COLOMBO, L ;
GENNARI, C ;
SCOLASTICO, C ;
GUANTI, G ;
NARISANO, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1278-1283
[4]   COMPLEMENTARITY OF (4+2) CYCLOADDITION REACTIONS AND [2,3] SIGMATROPIC REARRANGEMENTS IN SYNTHESIS - NEW SYNTHESIS OF FUNCTIONALIZED HASUBANAN DERIVATIVES [J].
EVANS, DA ;
SIMS, CL ;
BRYAN, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (08) :2891-&
[6]   ENANTIOFACE DIFFERENTIATING ASYMMETRIC REACTION BY PARA-TOLYLSULFINYLCARBANION [J].
KUNIEDA, N ;
KINOSHITA, M ;
NOKAMI, J .
CHEMISTRY LETTERS, 1977, (03) :289-292
[7]   BETA-DISULFOXIDES .2. PREPARATION OF SOME OPTICALLY-ACTIVE BETA-DISULFOXIDES [J].
KUNIEDA, N ;
NOKAMI, J ;
KINOSHITA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (01) :256-259
[8]   ASYMMETRICAL SYNTHESIS OF BETA-HYDROXY ACIDS BY CONDENSATION OF CHIRAL ALPHA-SULFINYLESTER ENOLATE ANIONS ON CARBONYL-COMPOUNDS [J].
MIOSKOWSKI, C ;
SOLLADIE, G .
TETRAHEDRON, 1980, 36 (02) :227-236
[9]  
SOLLADIE G, 1985, NOUV J CHIM, V9, P21
[10]  
TSUCHIHASHI G, 1972, TETRAHEDRON LETT, P4605