Bifunctional iminophosphorane superbases: Potent organocatalysts for enantio- and diastereoselective Michael addition reactions

被引：16

作者：

Farley, Alistair J. M. ^{[1
]}

Jakubec, Pavol ^{[1
,2
]}

Goldys, Anna M. ^{[1
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Mansfield Rd, Oxford OX1 3TA, England

[2] Slovak Univ Technol Bratislava, Fac Chem & Food Technol, Dept Organ Chem, Radlinskeho 9, SK-81237 Bratislava, Slovakia

来源：

TETRAHEDRON | 2018年 / 74卷 / 38期

基金：

英国工程与自然科学研究理事会;

关键词：

Asymmetric organocatalysis; Nitroolefin; Michael addition; Superbase; BIMP; Nakadomarin A; Continuous flow; RING-CLOSING METATHESIS; AZA-HENRY REACTION; ASYMMETRIC CATALYSIS; CHIRAL GUANIDINE; 1,4-ADDITION REACTION; CONJUGATE ADDITIONS; POLYSTYRYL-BEMP; CONTINUOUS-FLOW; ESTERS; ALPHA;

D O I：

10.1016/j.tet.2018.06.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bifunctional iminophosphorane (BIMP) organocatalysts catalyze the enantio- and diastereoselective Michael additions of high pK(a) cyclic malonamate ester pro-nucleophiles to nitroalkenes with reactivity profiles of up to 3 orders of magnitude greater than tertiary amine bifunctional Bronsted base/(thio)urea organocatalysts. The unrivalled performance of the BIMPs allows reaction times of challenging reactions to be slashed from weeks to minutes and has enabled new flow chemistry applications using polystyrene-supported versions contained within a flow reactor. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：5206 / 5212

页数：7

共 83 条

[1] Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions [J].

Andres, Jose M. ;

Ceballos, Miriam ;

Maestro, Alicia ;

Sanz, Isabel ;

Pedrosa, Rafael .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 :628-635

[2] E-Factor minimized hydrophosphonylation of aldehydes catalyzed by polystyryl-BEMP under solvent-free conditions [J].

Angelini, Tommaso ;

Bonollo, Simona ;

Lanari, Daniela ;

Pizzo, Ferdinando ;

Vaccaro, Luigi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (30) :5042-5046

[3] Asymmetric Organocatalysis in Continuous Flow: Opportunities for Impacting Industrial Catalysis [J].

Atodiresei, Iuliana ;

Vila, Carlos ;

Rueping, Magnus .

ACS CATALYSIS, 2015, 5 (03) :1972-1985

[4] Hydrogen bonding mediated enantioselective organocatalysis in brine: significant rate acceleration and enhanced stereoselectivity in enantioselective Michael addition reactions of 1,3-dicarbonyls to β-nitroolefins [J].

Bae, Han Yong ;

Some, Surajit ;

Oh, Joong Suk ;

Lee, Yong Seop ;

Song, Choong Eui .

CHEMICAL COMMUNICATIONS, 2011, 47 (34) :9621-9623

[5] Structure-activity relationship studies of cyclopropenimines as enantioselective Bronsted base catalysts [J].

Bandar, Jeffrey S. ;

Barthelme, Alexandre ;

Mazori, Alon Y. ;

Lambert, Tristan H. .

CHEMICAL SCIENCE, 2015, 6 (02) :1537-1547

[6] Cyclopropenimine-Catalyzed Enantioselective Mannich Reactions of tert-Butyl Glycinates with N-Boc-Imines [J].

Bandar, Jeffrey S. ;

Lambert, Tristan H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11799-11802

[7] Enantioselective Bronsted Base Catalysis with Chiral Cyclopropenimines [J].

Bandar, Jeffrey S. ;

Lambert, Tristan H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5552-5555

[8]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[9] Organocatalysis-after the gold rush [J].

Bertelsen, Soren ;

Jorgensen, Karl Anker .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189

[10]

Bonfils F, 2006, ORG BIOMOL CHEM, V4, P493, DOI 10.1039/b515241k

← 1 2 3 4 5 6 7 8 9 →