THE RHODIUM-CATALYZED HYDROBORATION OF OLEFINS - A MECHANISTIC INVESTIGATION

被引:81
作者
EVANS, DA
FU, GC
机构
[1] Department of Chemistry, Harvard University, Cambridge
关键词
D O I
10.1021/jo00295a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Labeling studies carried out on the rhodium-catalyzed olefin hydroboration reaction reveal that the degree of reversibility of the elementary steps in the catalytic cycle is highly substrate dependent. The implications of these observations are discussed. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:2280 / 2282
页数:3
相关论文
共 20 条
[1]   SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITY IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ALLYLIC AMINE DERIVATIVES [J].
BURGESS, K ;
OHLMEYER, MJ .
TETRAHEDRON LETTERS, 1989, 30 (43) :5857-5860
[2]   DIASTEREOCONTROL IN RHODIUM-CATALYZED HYDROBORATION OF CHIRAL ACYCLIC ALLYLIC ALCOHOL DERIVATIVES [J].
BURGESS, K ;
OHLMEYER, MJ .
TETRAHEDRON LETTERS, 1989, 30 (04) :395-398
[3]   ON CATALYZED AND UNCATALYZED HYDROBORATIONS OF CHIRAL ALLYLIC ALCOHOLS AND AMINES [J].
BURGESS, K ;
OHLMEYER, MJ .
TETRAHEDRON LETTERS, 1989, 30 (43) :5861-5864
[4]   ENANTIOSELECTIVE HYDROBORATION MEDIATED BY HOMOCHIRAL RHODIUM CATALYSTS [J].
BURGESS, K ;
OHLMEYER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5178-5179
[5]   MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].
CHAMBERLIN, AR ;
MULHOLLAND, RL ;
KAHN, SD ;
HEHRE, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677
[6]  
COLLMAN JP, 1987, PRINCIPLES APPLICATI
[7]   HYDROFORMYLATION OF TRICARBONYL(ETA-6-STYRENE)CHROMIUM AND RELATED-COMPOUNDS [J].
DOYLE, MM ;
JACKSON, WR ;
PERLMUTTER, P .
TETRAHEDRON LETTERS, 1989, 30 (39) :5357-5360
[8]   RHODIUM(I)-CATALYZED HYDROBORATION OF OLEFINS - THE DOCUMENTATION OF REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN CYCLIC AND ACYCLIC SYSTEMS [J].
EVANS, DA ;
FU, GC ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6917-6918
[9]   MECHANISM AND STEREOSELECTIVITY OF ASYMMETRIC HYDROGENATION [J].
HALPERN, J .
SCIENCE, 1982, 217 (4558) :401-407
[10]   CATALYTIC ASYMMETRIC HYDROBORATION OF STYRENES [J].
HAYASHI, T ;
MATSUMOTO, Y ;
ITO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3426-3428