Synthesis of isoxazolidines via catalyst-free one-pot three-component cycloaddition of sulfoxonium ylides, nitrosoarenes and alkenes

被引:28
作者
Li, Xing [1 ]
Zhai, Pingan [1 ]
Fang, Yongsheng [1 ]
Li, Wenhui [1 ]
Chang, Honghong [1 ]
Gao, Wenchao [1 ]
机构
[1] Taiyuan Univ Technol, Coll Biomed Engn, 79 West Yingze St, Taiyuan 030024, Peoples R China
关键词
ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; BICYCLIC ISOXAZOLIDINES; NITRONE; CASCADE; ACCESS; ENHANCEMENT; ANNULATIONS; SELECTIVITY; GENERATION;
D O I
10.1039/d0qo01471k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and practical strategy for the construction of various keto-substituted isoxazolidines via one-pot three-component reaction of easily accessible, safer and more stable sulfoxonium ylides, nitrosoarenes and olefins is described. This three-component approach features remarkably much broader substrate scope, good functional group tolerance, good to high yields, operational safety and mild reaction conditions, and this method is also catalyst-free, additive-free and operationally simple.
引用
收藏
页码:988 / 995
页数:8
相关论文
共 79 条
[1]   Microwave-assisted cycloaddition reactions [J].
Appukkuttan, Prasad ;
Mehta, Vaibhav P. ;
Van der Eycken, Erik V. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (05) :1467-1477
[2]   N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones [J].
Atienza, Roxanne L. ;
Roth, Howard S. ;
Scheidt, Karl A. .
CHEMICAL SCIENCE, 2011, 2 (09) :1772-1776
[3]   Nitrone Cycloadditions of 1,2-Cyclohexadiene [J].
Barber, Joyann S. ;
Styduhar, Evan D. ;
Pham, Hung V. ;
McMahon, Travis C. ;
Houk, K. N. ;
Garg, Neil K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (08) :2512-2515
[4]   Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].
Barday, Manuel ;
Janot, Christopher ;
Halcovitch, Nathan R. ;
Muir, James ;
Aissa, Christophe .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121
[5]   Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry [J].
Berthet, Matheo ;
Cheviett, Thomas ;
Dujardin, Gilles ;
Parrot, Isabelle ;
Martinez, Jean .
CHEMICAL REVIEWS, 2016, 116 (24) :15235-15283
[6]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269
[7]   Enantioselective 1,3-dipolar cycloaddition of nitrones to methacrolein catalyzed by (η5-C5Me5)M{(R)-Prophos} containing complexes (M = Rh, Ir;: (R)-Prophos=1,2-bis(diphenylphosphino)propane):: On the origin of the enantioselectivity [J].
Carmona, D ;
Lamata, MP ;
Viguri, F ;
Rodríguez, R ;
Oro, LA ;
Lahoz, FJ ;
Balana, AI ;
Tejero, T ;
Merino, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13386-13398
[8]   Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines [J].
Chakrabarty, Shyamal ;
Chatterjee, Indranil ;
Wibbeling, Birgit ;
Daniliuc, Constantin Gabriel ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) :5964-5968
[9]   Water exclusion reaction in aqueous media: Nitrone formation and cycloaddition in a single pot [J].
Chatterjee, A ;
Maiti, DK ;
Bhattacharya, PK .
ORGANIC LETTERS, 2003, 5 (21) :3967-3969
[10]   Formation of Isoxazolidines by Enantioselective Copper-Catalyzed Annulation of 2-Nitrosopyridine with Allylstannanes [J].
Chatterjee, Indranil ;
Froehlich, Roland ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11257-11260