ACTIVATION OF KETENE SILYL ACETALS BY 10-METHYLACRIDINIUM PERCHLORATE - A NOVEL CATALYSIS IN MUKAIYAMA REACTION

被引：24

作者：

OTERA, J ^{[1
]}

WAKAHARA, Y ^{[1
]}

KAMEI, H ^{[1
]}

SATO, T ^{[1
]}

NOZAKI, H ^{[1
]}

FUKUZUMI, S ^{[1
]}

机构：

[1] OSAKA UNIV,FAC ENGN,DEPT APPL CHEM,SUITA,OSAKA 565,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)79935-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

10-Methylacridinium perchlorate (1) effectively promotes various reactions of ketene silyl acetals: aldol and Michael addition products are obtained with aldehydes, ketones, acetals, and alpha-enones. The reactions exhibit unusual dependency upon 1, namely the yields are excellent when a catalytic amount of 1 is employed whereas no desired products are accessible by the use of 1 in a stoichiometric quantity. A novel catalytic cycle is proposed.

引用

页码：2405 / 2408

页数：4

共 50 条

[1] Mukaiyama aldol reaction using ketene silyl acetals with carbonyl compounds in ionic liquids
Chen, SL
Ji, SJ
Loh, TP
TETRAHEDRON LETTERS, 2004, 45 (02) : 375 - 377
[2] The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters
Gatzenmeier, Tim
Kaib, Philip S. J.
Lingnau, Julia B.
Goddard, Richard
List, Benjamin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2464 - 2468
[3] A Novel Reaction of 10-Methylacridinium with Reactive Metals under Grinding
Xu, Huajian
Xu, Xiaolan
Feng, Yisi
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (02) : 289 - 291
[4] Mukaiyama aldol reaction of ester acceptors: Organoaluminums catalyze nucleophilic addition of ketene silyl acetals
Iwata, Shin
Hamura, Toshiyuki
Matsumoto, Takashi
Suzuki, Keisuke
CHEMISTRY LETTERS, 2007, 36 (04) : 538 - 539
[5] Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones
Bae, Han Yong
List, Benjamin
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (52) : 13767 - 13772
[6] HIGHLY EFFECTIVE CATALYSTS FOR THE CONJUGATE ADDITION OF SILYL KETENE ACETALS TO ENONES (MUKAIYAMA-MICHAEL REACTION)
BERL, V
HELMCHEN, G
PRESTON, S
TETRAHEDRON LETTERS, 1994, 35 (02) : 233 - 236
[7] REACTION OF ETHYL AZIDOFORMATE WITH KETENE SILYL ACETALS
CIPOLLONE, A
LORETO, MA
PELLACANI, L
TARDELLA, PA
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12): : 2584 - 2586
[8] THE REACTION OF A 10-METHYLACRIDINIUM SALT WITH TERTIARY-AMINES
TAMAGAKI, S
UENO, M
TAGAKI, W
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (01) : 55 - 60
[9] IMPORTANCE OF LEWIS ACID MEDIATED ELECTRON-TRANSFER IN MUKAIYAMA-MICHAEL REACTION OF KETENE SILYL ACETALS
SATO, T
WAKAHARA, Y
OTERA, J
NOZAKI, H
FUKUZUMI, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) : 4028 - 4030
[10] Reaction of nitrones with silyl ketene acetals: A DFT study
Milet, A
Gimbert, Y
Greene, AE
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2006, 27 (02) : 157 - 162

← 1 2 3 4 5 →