Homogeneous catalysis. Mechanisms of the catalysed Mukaiyama cross-aldol reaction

被引：12

作者：

Ellis, WW ^{[1
]}

Bosnich, B ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 02期

关键词：

D O I：

10.1039/a705801b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

It is shown that [2 + 2] addition intermediates can form reversibly in the catalysed Mukaiyama reaction; these serve to prevent formation of the catalyst Me3Si+ and the reactivities of the [2 + 2] intermediates can affect the enantioselectivity of the reaction.

引用

页码：193 / 194

页数：2

共 33 条

[1] ABEN RW, 1978, SYNTHESIS-STUTTGART, P400
[2] CATIONIC MONONUCLEAR AND BINUCLEAR IRON COMPLEXES AS LEWIS ACID CATALYSTS IN MUKAIYAMA REACTIONS
BACH, T
FOX, DNA
REETZ, MT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) : 1634 - 1636
[3] STEREOSELECTIVE PHOTOCYCLOADDITION OF SILYL ENOL ETHERS TO ALDEHYDES - CONFIGURATIONAL CONTROL OF 3 STEREOGENIC CENTERS IH OXETANES
BACH, T
[J]. TETRAHEDRON LETTERS, 1994, 35 (32) : 5845 - 5848
[4] METAL VERSUS SILYL TRIFLATE CATALYSIS IN THE MUKAIYAMA ALDOL ADDITION-REACTION
CARREIRA, EM
SINGER, RA
[J]. TETRAHEDRON LETTERS, 1994, 35 (25) : 4323 - 4326
[5] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV)
CARREIRA, EM
SINGER, RA
LEE, WS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8837 - 8838
[6] ASYMMETRICAL SYNTHESIS OF BETA-HYDROXY ESTERS BY REFORMATSKY REACTION IN PRESENCE OF (-) SPARTEINE
GUETTE, M
CAPILLON, J
GUETTE, JP
[J]. TETRAHEDRON, 1973, 29 (22) : 3659 - 3667
[7] [1,2-BENZENEDIOLATO(2-)-O-O']OXOTITANIUM - A CHEMOSELECTIVE AND EFFICIENT CATALYST FOR ALDOL-TYPE REACTION OF KETENE SILYL ACETALS WITH ALDEHYDES
HARA, R
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1989, (11) : 1909 - 1912
[8] HOMOGENEOUS CATALYSIS - MECHANISMS OF THE CATALYTIC MUKAIYAMA ALDOL AND SAKURAI ALLYLATION REACTIONS
HOLLIS, TK
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) : 4570 - 4581
[9] AN ESSENTIALLY MILD AND EFFICIENT CATALYST SYSTEM FOR THE ACTIVATION OF CARBONYL-COMPOUNDS AND THEIR DERIVATIVES - THE COMBINED USE OF TRIMETHYLSILYL CHLORIDE AND TIN(II) CHLORIDE
IWASAWA, N
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1987, (03) : 463 - 466
[10] KOBAYASHI S, 1993, SYNTHESIS-STUTTGART, P371

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