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

[1] Intramolecular cycloaddition of O-tert-butyldimethylsilyloximes in the presence of BF3•OEt2
Tamura, O
Mitsuya, T
Huang, X
Tsutsumi, Y
Hattori, S
Ishibashi, H
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26): : 10720 - 10725
[2] BF3•OEt2 promoted selective synthesis of benzimidazoles
Rajanarendar, E.
Ramesh, P.
Rao, E. Kalyan
Mohan, G.
Reddy, A. Siva Rami
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) : 1153 - 1159
[3] BF3 . OEt2 Catalyzed Synthesis of 1,3-Thiazines/-Selenazines
Muthusamy, Sengodagounder
Malarvizhi, Muthukumar
Suresh, Eringathodi
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (01) : 170 - 175
[4] BF3•OEt2: An Efficient Catalyst for Transesterification of β-Ketoesters
Yang, Jinhui
Ji, Congbin
Zhao, Yanmin
Li, Yunfeng
Jiang, Shizhi
Zhang, Zhiwei
Ji, Yongqiang
Liu, Wanyi
SYNTHETIC COMMUNICATIONS, 2010, 40 (07) : 957 - 963
[5] Sulfination of alcohols with sodium sulfinates promoted by BF3•OEt2: an unexpected access
Huang, Mingming
Hu, Liangzhen
Shen, Hang
Liu, Qing
Hussain, Muhammad Ijaz
Pan, Jing
Xiong, Yan
GREEN CHEMISTRY, 2016, 18 (07) : 1874 - 1879
[6] BF3•OEt2 Mediated Intramolecular Cyclization of 2-Alkynylanilines
Gao, Yushen
Gao, Yuanyuan
Zhang, An'an
Li, Lu
Geng, Weizhi
Zhang, Fenghua
Li, Fei
Liu, Lantao
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (09) : 2785 - 2795
[7] BF3•OEt2 and TMSOTf:: A synergistic combination of Lewis acids
Myers, Eddie L.
Butts, Craig P.
Aggarwal, Varinder K.
CHEMICAL COMMUNICATIONS, 2006, (42) : 4434 - 4436
[8] Ring opening reactions of cyclic α,β-epoxysilanes with BF3•OEt2
Kira, K
Isobe, H
CHEMISTRY LETTERS, 2001, (05) : 432 - 433
[9] Application of BF3•OEt2 in Organic Synthesis as a Catalyst or Synthon
Chen Zujia
Yu Shiwei
Zhou Yongjun
Li Huanqing
Qiu Qiwen
Li Miaoxin
Wang Zhaoyang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (09) : 3107 - 3118
[10] BF3 ⋅ OEt2 as a Versatile Reagent: Applications in Organic Synthesis
Kumar, Sumit
Arora, Aditi
Chaudhary, Riya
Sapra, Shivani
Shankar, Bhawani
Kumar, Sandeep
Singh, Brajendra K.
CHEMISTRYSELECT, 2024, 9 (41):

← 1 2 3 4 5 →