Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides

被引：57

作者：

Toda, Yasunori ^{[1
]}

Gomyou, Shuto ^{[1
]}

Tanaka, Shoya ^{[1
]}

Komiyama, Yutaka ^{[1
]}

Kikuchi, Ayaka ^{[1
]}

Suga, Hiroyuki ^{[1
]}

机构：

[1] Shinshu Univ, Dept Mat Chem, Fac Engn, 4-17-1 Wakasato, Nagano 3808553, Japan

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 21期

基金：

日本学术振兴会;

关键词：

CARBON-DIOXIDE; TETRAPHENYLSTIBONIUM IODIDE; MGI2; ETHERATE; SELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; CHIRAL AUXILIARIES; ACETYLENIC AMINES; IONIC LIQUIDS; CYCLOADDITION; OXIRANES;

D O I：

10.1021/acs.orglett.7b02722

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preparation of a range of oxazolidinones, including enantioenriched N-aryl-substituted oxazolidinones, in which tetraarylphosphonium salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates and epoxides effectively, is described. The key finding is a Bronsted acid/halide ion bifunctional catalyst that can accelerate epoxide ring opening with high regioselectivity. Mechanistic studies disclosed that the ylide generated from TAPS, along with the formation of halohydrins, plays a crucial role in the reaction with isocyanates.

引用

页码：5786 / 5789

页数：4

共 50 条

[1] 4-Hydroxymethyl-substituted oxazolidinone synthesis by tetraarylphosphonium salt-catalyzed reactions of glycidols with isocyanates
Toda, Yasunori
Tanaka, Shoya
Gomyou, Shuto
Kikuchi, Ayaka
Suga, Hiroyuki
[J]. CHEMICAL COMMUNICATIONS, 2019, 55 (41) : 5761 - 5764
[2] Bimetallic Aluminum(salen) Catalyzed Synthesis of Oxazolidinones from Epoxides and Isocyanates
Baronsky, Thilo
Beattie, Christopher
Harrington, Ross W.
Irfan, Reyhan
North, Michael
Osende, Javier G.
Young, Carl
[J]. ACS CATALYSIS, 2013, 3 (04): : 790 - 797
[3] Tetraarylphosphonium salt-catalyzed formal [3+2] cycloaddition between epoxides and trichloroacetonitrile for the synthesis of β-amino alcohol derivatives
Toda, Yasunori
Shiokawa, Ryota
Iwasaki, Masaya
Yamaguchi, Daisuke
Kawamura, Keisuke
Sukegawa, Kimiya
Suga, Hiroyuki
[J]. CHEMICAL COMMUNICATIONS, 2022, 58 (84) : 11819 - 11822
[4] Samarium triiodide catalyzed cycloaddition of epoxides with isocyanates : a facile synthesis of oxazolidinones
Wu, HY
Ding, JC
Liu, YK
[J]. JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2003, 80 (01) : 36 - 37
[5] Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalyzed by Rare-Earth-Metal Complexes
Wang, Peng
Qin, Jie
Yuan, Dan
Wang, Yaorong
Yao, Yingming
[J]. CHEMCATCHEM, 2015, 7 (07) : 1145 - 1151
[6] Tetraarylphosphonium Salt-Catalyzed Carbon Dioxide Fixation at Atmospheric Pressure for the Synthesis of Cyclic Carbonates
Toda, Yasunori
Komiyama, Yutaka
Kikuchi, Ayaka
Suga, Hiroyuki
[J]. ACS CATALYSIS, 2016, 6 (10): : 6906 - 6910
[7] A FACILE SYNTHESIS OF OXAZOLIDINONES VIA LANTHANIDE-CATALYZED CYCLOADDITION OF EPOXIDES WITH ISOCYANATES
QIAN, CT
ZHU, DM
[J]. SYNLETT, 1994, (02) : 129 - 130
[8] VanadiumV(salen) catalysed synthesis of oxazolidinones from epoxides and isocyanates
Beattie, Christopher
North, Michael
[J]. RSC ADVANCES, 2014, 4 (59) : 31345 - 31352
[9] Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalysed by Aluminium Heteroscorpionate Complexes
Castro-Osma, Jose A.
Earlam, Amy
Lara-Sanchez, Agustin
Otero, Antonio
North, Michael
[J]. CHEMCATCHEM, 2016, 8 (12) : 2100 - 2108
[10] [(Salcen)CrIII + Lewis base]-catalyzed synthesis of N-aryl-substituted oxazolidinones from epoxides and aryl isocyanates
Paddock, Robert L.
Adhikari, Debashis
Lord, Richard L.
Baik, Mu-Hyun
Nguyen, SonBinh T.
[J]. CHEMICAL COMMUNICATIONS, 2014, 50 (96) : 15187 - 15190

← 1 2 3 4 5 →