Access of cis-4-monofluoromethyl-1,3-oxazolidines via a formal [3+2] cycloaddition triggered by BF3•OEt2

被引：1

作者：

Sato, Keiichi ^{[1
]}

Yamada, Yasunori ^{[1
]}

Hanamoto, Takeshi ^{[1
]}

机构：

[1] Saga Univ, Dept Chem & Appl Chem, Honjyo Machi 1, Saga 8408502, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2020年 / 237卷

关键词：

Organofluorine; Monofluoromethyl group (CFH2); Aziridine; Oxazolidine; Cycloaddition; ONE-POT SYNTHESIS; 2-TRIFLUOROMETHYL-N-TOSYLAZIRIDINE; AZIRIDINE; FLUORINE;

D O I：

10.1016/j.jfluchem.2020.109599

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of cis-4-monofluoromethyl-1,3-oxazolidines were prepared from 2-monofluoromethyl-N-tosylaziridine and various aldehydes in the presence of (BF3OEt2)-O-center dot under mild conditions. The high regioselectivity of the reaction suggested that the electron-withdrawing ability of the monofluoromethyl group is similar to that of trifluoromethyl and difluoromethyl groups in this type of cycloaddition.

引用

页数：6

共 50 条

[41] Glycosylation of sialyl acetates with a novel catalyst combination:: Bismuth triflate and BF3•OEt2 system
Ikeda, K
Torisawa, Y
Nishi, T
Minamikawa, J
Tanaka, K
Sato, M
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (14) : 3073 - 3076
[42] BF3 ⋅ OEt2 and Visible Light-Controlled [3,3]- or [1,3]-Rearrangement of Quinazolinone N-O Aryl Moieties
Nie, Shu-Min
Cheng, Lu-Min
Chen, Chun-Hua
Liang, Cui
Pan, Cheng-Xue
Mo, Dong-Liang
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (09) : 2056 - 2062
[43] Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3•OEt2
Erturk, Erkan
Tezeren, Mustafa A.
Atalar, Taner
Tilki, Tahir
TETRAHEDRON, 2012, 68 (32) : 6463 - 6471
[44] BF3•OEt2-initiated polymerization of 2-methylene-1,3-dioxepanes
Wu, ZH
Pittman, CU
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1998, 36 (06) : 873 - 881
[45] COORDINATION POLYMERIZATION OF 1,3-BUTADIENE WITH Ni(naph)2/A1R3/BF3•OEt2/DMEA/OctOH CATALYST SYSTEM
Qiao Yulu
Zhu Han
Wu Yixian
Wang Jin
Xu Riwei
Wu Guanying
Yang Wantai
ACTA POLYMERICA SINICA, 2010, (06) : 640 - 646
[46] New olefination of acetals with TMSCH2Cu(PBu3)•LiI under the influence of BF3•OEt2
Suzuki, T
Oriyama, T
SYNLETT, 2000, (06) : 859 - 861
[47] Role of temperature in [3+2]-cycloaddition of isoselenocyanates with oxiranes using BF3•Et2O
Sengoden, Mani
Punniyamurthy, Tharmalingam
RSC ADVANCES, 2012, 2 (07): : 2736 - 2738
[48] Unique synthetic utility of BF3•OEt2 in the highly diastereoselective reduction of hydroxy carbonyl and dicarbonyl substrates
Ooi, T
Uraguchi, D
Morikawa, J
Maruoka, K
ORGANIC LETTERS, 2000, 2 (14) : 2015 - 2017
[49] An efficient selective reduction of aromatic azides to amines employing BF3•OEt2/NaI:: Synthesis of pyrrolobenzodiazepines
Kamal, Ahmed
Shankaraiah, N.
Markandeya, N.
Reddy, Ch. Sanjeeva
SYNLETT, 2008, (09) : 1297 - 1300
[50] Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3•OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates
Cao, Liang
Luo, Shi-He
Jiang, Kai
Hao, Zhi-Feng
Wang, Bo-Wen
Pang, Chu-Ming
Wang, Zhao-Yang
ORGANIC LETTERS, 2018, 20 (16) : 4754 - 4758

← 1 2 3 4 5 →