ASYMMETRIC HYDROFORMYLATIONS OF SULFUR-CONTAINING OLEFINS CATALYZED BY BINAPHOS-RH(I) COMPLEXES

被引:48
作者
NANNO, T [1 ]
SAKAI, N [1 ]
NOZAKI, K [1 ]
TAKAYA, K [1 ]
机构
[1] KYOTO UNIV,GRAD SCH ENGN,DEPT CHEM MAT,SAKYO KU,KYOTO 60601,JAPAN
关键词
D O I
10.1016/0957-4166(95)00339-Q
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric hydroformylations of vinyl sulfides, allyl sulfides, and allyl sulfones catalyzed by (R,S)-BINAPHOS/Rh(acac)(CO)(2) afforded the corresponding branched oxo aldehydes as major products in 60-89% ee. Use of bulkier substituents on the sulfur in vinyl sulfides gave the branched oxo-aldehydes in higher regio- and enantioselectivities.
引用
收藏
页码:2583 / 2591
页数:9
相关论文
共 17 条
[1]   TOTAL SYNTHESIS OF (+)-MILBEMYCIN-BETA-3 [J].
BAKER, R ;
OMAHONY, MJ ;
SWAIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07) :1623-1633
[2]   ADVANCES IN THE HYDROFORMYLATION OF OLEFINS CONTAINING FUNCTIONAL-GROUPS [J].
BOTTEGHI, C ;
GANZERLA, R ;
LENARDA, M ;
MORETTI, G .
JOURNAL OF MOLECULAR CATALYSIS, 1987, 40 (02) :129-182
[3]  
BOTTEGHI C, 1991, CHIRALITY, V3, P335
[4]   FORMATION OF CIS-FUSED CYCLOPENTANOIDS BY MICHAEL ADDITION AND RADICAL CYCLIZATION [J].
CLIVE, DLJ ;
BOIVIN, TLB .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1997-2003
[5]   PLATINUM-CATALYZED ENANTIOSELECTIVE HYDROFORMYLATION WITH (R,R)-[BICYCLO[2.2.2]OCTANE-2,3-DIYLBIS(METHYLENE)]BIS(5H-BENZO[B]PHOSPHINDOLE) AND RELATED CHIRAL LIGANDS [J].
CONSIGLIO, G ;
NEFKENS, SCA ;
BORER, A .
ORGANOMETALLICS, 1991, 10 (06) :2046-2051
[6]   SYNTHESIS OF NEW CHIRAL PHOSPHINEPHOSPHITES HAVING 2-DIPHENYLPHOSPHINOBIPHENYL-2'-YL BACKBONE AND THEIR USE IN RH(I)-CATALYZED ASYMMETRIC HYDROFORMYLATIONS [J].
HIGASHIZIMA, T ;
SAKAI, N ;
NOZAKI, K ;
TAKAYA, H .
TETRAHEDRON LETTERS, 1994, 35 (13) :2023-2026
[7]  
HORIUCHI T, UNPUB
[8]   RHODIUM-CATALYZED LOW-PRESSURE HYDROFORMYLATION OF SUBSTITUTED TERMINAL OLEFINS - ROLE OF ALPHA,OMEGA-BIS(DIPHENYLPHOSPHINO)ALKANE IN COMBINATION WITH EXCESS TRIPHENYLPHOSPHINE [J].
MATSUMOTO, M ;
TAMURA, M .
JOURNAL OF MOLECULAR CATALYSIS, 1982, 16 (02) :195-207
[9]  
NANNO T, IN PRESS
[10]   1ST ASYMMETRIC-SYNTHESIS OF ENANTIOPURE ALPHA-SULFENYL DITHIOACETALS AND ALPHA-SULFENYL ALDEHYDES [J].
POLI, G ;
BELVISI, L ;
MANZONI, L ;
SCOLASTICO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3165-3168