Recent advances in asymmetric phosphine oxide catalysis

被引:21
作者
Kotani, Shunsuke [1 ]
Nakajima, Makoto [1 ]
机构
[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 5-1 Oe Honmachi, Kumamoto 8620973, Japan
基金
日本学术振兴会;
关键词
Aldol reaction; Enantioselectivity; Halocyclization; Phosphine oxide; Sequential catalysis; ABRAMOV-TYPE PHOSPHONYLATION; PYRIDINE N-OXIDES; BIHETEROAROMATIC DIPHOSPHINE OXIDES; ENANTIOSELECTIVE ALDOL REACTIONS; LEWIS-BASE ACTIVATION; MESO-EPOXIDES; STEREOSELECTIVE-SYNTHESIS; TRICHLOROSILYL TRIFLATE; AZIRIDINYL PHOSPHONATE; SILICON TETRACHLORIDE;
D O I
10.1016/j.tetlet.2019.151421
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phosphine oxides are versatile catalysts in organic synthesis and mediate a broad range of transformations. In this digest, we review the recent developments in phosphine oxide-catalyzed asymmetric reactions. The enantioselective double aldol reactions, enantioselective aldol reaction of carboxylic acids, and enantioselective halocyclizations are discussed. These novel phosphine oxide-catalyzed processes are vital for the stereoselective synthesis and functionalization of useful organic molecules and intermediates. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:8
相关论文
共 94 条
[1]   Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst [J].
Aoki, Shohei ;
Kotani, Shunsuke ;
Sugiura, Masaharu ;
Nakajima, Makoto .
CHEMICAL COMMUNICATIONS, 2012, 48 (44) :5524-5526
[2]   Enantioselective reactions catalyzed by phosphine oxides [J].
Ayad, Tahar ;
Gernet, Aurelie ;
Pirat, Jean-Luc ;
Virieux, David .
TETRAHEDRON, 2019, 75 (33) :4385-4418
[3]   Stereoselective reactions involving hypervalent silicate complexes [J].
Benaglia, Maurizio ;
Guizzetti, Stefania ;
Pignataro, Luca .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :492-512
[4]   Chiral phosphine oxides in present-day organocatalysis [J].
Benaglia, Maurizio ;
Rossi, Sergio .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (17) :3824-3830
[5]   Diarylnonanoids and their glucosides from Erica cinerea [J].
Bennini, Bachir ;
Chulia, Albert J. ;
Kaouadji, Mourad ;
Fondaneche, Patrice ;
Allais, Daovy P. .
TETRAHEDRON LETTERS, 2011, 52 (14) :1597-1600
[6]   Synthesis, Characterisation, and Organocatalytic Activity of Chiral Tetrathiahelicene Diphosphine Oxides [J].
Cauteruccio, Silvia ;
Dova, Davide ;
Benaglia, Maurizio ;
Genoni, Andrea ;
Orlandi, Manuel ;
Licandro, Emanuela .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (13) :2694-2702
[7]   Synthesis of axially chiral C10-BridgePHOS oxides and their use as organocatalysts in enantioselective allylations of aldehydes [J].
Chen, Jianzhong ;
Liu, Delong ;
Fan, Dongyang ;
Liu, Yangang ;
Zhang, Wanbin .
TETRAHEDRON, 2013, 69 (38) :8161-8168
[8]   Helical Chiral Pyridine N-Oxides: A New Family of Asymmetric Catalysts [J].
Chen, Jinshui ;
Takenaka, Norito .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (30) :7268-7276
[9]   Air-stable P-stereogenic secondary phosphine oxides as chiral monodentate ligands for asymmetric catalytic carbon-carbon bond formation [J].
Dai, WM ;
Yeung, KKY ;
Leung, WH ;
Haynes, RK .
TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2821-2826
[10]   Lewis base catalysis in organic synthesis [J].
Denmark, Scott E. ;
Beutner, Gregory L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638