Asymmetric Halocyclization of 2-Anilidostyrenes Using N-Haloamides Enabled by Chiral Anion Phase-Transfer Catalysis

被引：0

作者：

Zhang, Penglei ^{[1
]}

Du, Xue ^{[1
]}

Tu, Guogang ^{[1
]}

Sun, Yanji ^{[1
]}

Xiong, Xiaodong ^{[1
]}

机构：

[1] Nanchang Univ, Sch Pharm, Nanchang 330006, Peoples R China

来源：

ORGANIC LETTERS | 2025年

基金：

中国国家自然科学基金;

关键词：

INHIBITORS; FLUORINE; ALCOHOLS; POTENT;

D O I：

10.1021/acs.orglett.5c00887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric halogenation for efficient construction of various 4H-3,1-benzoxazine derivatives with excellent functional group tolerance using readily available N-haloamides as the halogen source and ammonium phosphate salt catalyst under mild reaction conditions has been developed. The ammonium salt catalyst loading could be reduced to 1 mol % and recycled 4 times without deterioration in reactivity and stereoselectivity. Importantly, this process features a column-purification-free operation, leading to the green and atom-economical preparation of chiral benzoxazines in good to excellent yields and high enantioselectivities.

引用

页数：6

共 50 条

[21] Synthesis of asymmetric N-arylaziridine derivatives using a new chiral phase-transfer catalyst
Murugan, E
Siva, A
SYNTHESIS-STUTTGART, 2005, (12): : 2022 - 2028
[22] Recent Asymmetric Phase-Transfer Catalysis with Chiral Binaphthyl-Modified and Related Phase-Transfer Catalysts over the Last 10 Years
Lee, Hyo-Jun
Maruoka, Keiji
CHEMICAL RECORD, 2023, 23 (07):
[23] ASYMMETRIC INDUCTION BY PHASE-TRANSFER CATALYSIS USING CHIRAL CATALYSTS - SYNTHESIS OF 1,2-DICHLOROALKANES AND ACETYLCYANOHYDRINS
JULIA, S
GINEBREDA, A
TETRAHEDRON LETTERS, 1979, (23) : 2171 - 2174
[24] Asymmetric Electrophilic Fluorination Using an Anionic Chiral Phase-Transfer Catalyst
Rauniyar, Vivek
Lackner, Aaron D.
Hamilton, Gregory L.
Toste, F. Dean
SCIENCE, 2011, 334 (6063) : 1681 - 1684
[25] Asymmetric phase-transfer catalysis of homo- and heterochiral quaternary ammonium salts: development and application of conformationally flexible chiral phase-transfer catalysts
Ooi, Takashi
Uematsu, Yukitaka
Kameda, Minoru
Maruoka, Keiji
TETRAHEDRON, 2006, 62 (49) : 11425 - 11436
[26] ORGN 505-Asymmetric acylimidazole alkylation using phase-transfer catalysis
Andrus, Merritt B.
Hicken, Erik J.
Bedke, David K.
Christiansen, Michael A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[27] Asymmetric permanganate-promoted oxidative cyclization of 1,5-dienes by using chiral phase-transfer catalysis
Brown, RCD
Keily, JF
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (23) : 4496 - +
[28] Asymmetric permanganate-promoted oxidative cyclization of 1,5-dienes by using chiral phase-transfer catalysis
Brown, R.C.D. (rcb1@soton.ac.uk), 2001, Wiley-VCH Verlag (40)
[29] Asymmetric Bromoaminocyclization and Desymmetrization of Cyclohexa-1,4-dienes through Anion Phase-Transfer Catalysis
Long, Hai-Jiao
Li, Yin-Long
Zhang, Bing-Qian
Xiao, Wen-Ying
Zhang, Xiao-Ying
He, Ling
Deng, Jun
ORGANIC LETTERS, 2021, 23 (21) : 8153 - 8157
[30] CONVENIENT SYNTHESIS OF N-ALKYLACRIDANONES USING PHASE-TRANSFER CATALYSIS
GALY, JP
ELGUERO, J
VINCENT, EJ
GALY, AM
BARBE, J
SYNTHESIS-STUTTGART, 1979, (12): : 944 - 946

← 1 2 3 4 5 →