Iron(II)-Catalyzed Intramolecular Olefin Aminofluorination

被引：77

作者：

Lu, Deng-Fu ^{[1
]}

Liu, Guan-Sai ^{[1
]}

Zhu, Cheng-Liang ^{[1
]}

Yuan, Bo ^{[1
]}

Xu, Hao ^{[1
]}

机构：

[1] Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 11期

关键词：

C-H FLUORINATION; ORGANOCATALYTIC ALPHA-FLUORINATION; PHASE-TRANSFER CATALYST; AMINO-ACID-DERIVATIVES; BETA-FLUOROAMINES; ASYMMETRIC-SYNTHESIS; UNACTIVATED ALKENES; ENANTIOSELECTIVE FLUORINATION; HYDROGEN-FLUORIDE; ARYL FLUORIDES;

D O I：

10.1021/ol501051p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iron(II)-catalyzed diastereoselective olefin aminofluorination is reported (dr up to >20:1). This new transformation applies a functionalized hydroxylamine and Et3N center dot 3HF as the nitrogen and fluorine source, which facilitates the efficient synthesis of beta-fluoro primary amines and amino acids from allylic alcohol derivatives. Preliminary mechanistic studies reveal that an iron-nitrenoid is a possible intermediate and that its reactivity and enantioselectivity can be efficiently modulated by ligands.

引用

收藏

页码：2912 / 2915

页数：4

相关论文

共 77 条

[1] Reversible C-F bond formation and the Au-catalyzed hydrofluorination of alkynes [J].

Akana, Jennifer A. ;

Bhattacharyya, Koyel X. ;

Mueller, Peter ;

Sadighi, Joseph P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7736-+

[2]

Al-Maharik N, 2011, ALDRICHIM ACTA, V44, P65

[3] RING-OPENING OF AZIRIDINES BY DIFFERENT FLUORINATING REAGENTS - 3 SYNTHETIC ROUTES TO ALPHA,BETA-FLUORO AMINES WITH DIFFERENT STEREOCHEMICAL PATHWAYS [J].

ALVERNHE, GM ;

ENNAKOUA, CM ;

LACOMBE, SM ;

LAURENT, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4938-4948

[4] Organocatalytic Enantioselective Olefin Aminofluorination [J].

Appayee, Chandrakumar ;

Brenner-Moyer, Stacey E. .

ORGANIC LETTERS, 2010, 12 (15) :3356-3359

[5] Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study [J].

Au, SM ;

Huang, JS ;

Yu, WY ;

Fung, WH ;

Che, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9120-9132

[6] Iron(II)-catalyzed intramolecular aminochlorination of alkenes [J].

Bach, T ;

Schlummer, B ;

Harms, K .

CHEMICAL COMMUNICATIONS, 2000, (04) :287-288

[7] Fe(III)/NaBH4-Mediated Free Radical Hydrofluorination of Unactivated Alkenes [J].

Barker, Timothy J. ;

Boger, Dale L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13588-13591

[8] Enantioselective organocatalytic α-fluorination of aldehydes [J].

Beeson, TD ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828

[9] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].

Begue, Jean-Pierre ;

Bonnet-Delpon, Daniele .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012

[10] A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination [J].

Bloom, Steven ;

Pitts, Cody Ross ;

Miller, David Curtin ;

Haselton, Nathan ;

Holl, Maxwell Gargiulo ;

Urheim, Ellen ;

Lectka, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) :10580-10583

← 1 2 3 4 5 6 7 8 →