Functionalized α-Fluorinated Amines from Imines and Enol Ethers

被引：1

作者：

Kyrko, Dimitra ^{[1
]}

Sarac, Murat ^{[1
]}

Hao, Jing ^{[1
]}

Retailleau, Pascal ^{[2
]}

Ongeri, Sandrine ^{[1
]}

Crousse, Benoit ^{[1
]}

机构：

[1] Univ Paris Saclay, CNRS, UMR 8076, BioCIS, Bldg Henri Moissan,17 Ave Sci, F-91400 Orsay, France

[2] Univ Paris Saclay, Inst Chim Subst Nat, CNRS, F-91198 Gif sur Yvette, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 16期

关键词：

Enol ethers; Amines; Fluoroalkyl groups; Amino alcohols; Pyrrolidines; ACID-DERIVATIVES; SILYL ACETAL; TRIFLUOROMETHYLATION; CHEMISTRY; ANALOGS; METHYL;

D O I：

10.1002/adsc.202400517

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report the addition reaction of lithium enol ethers to fluoroalkyl imines. A range of different fluoroalkyls and lithiated reagents are well tolerated. Diastereoselective addition of lithium vinyl ethers to fluoroalkyl N-tert-butylsulfinylimines is disclosed, providing enantiomerically enriched alpha-fluorinated amines in up to 98% yield. This general approach led to the diastereoselective formation of various amino alcohols and amino ethers, which are difficult to obtain by other methods. image

引用

页码：3460 / 3465

页数：6

共 50 条

[41] HIGHLY CONVENIENT ELECTROLYSIS PROCEDURE FOR THE PREPARATION OF ALPHA-HALOGENATED KETONES AND ACETALS FROM ENOL ACETATES, ENOL ETHERS, AND SILYL ENOL ETHERS
TORII, S
INOKUCHI, T
MISIMA, S
KOBAYASHI, T
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (13): : 2731 - 2735
[42] Reductive N-Arylethylation of Aromatic Amines and N-Heterocycles with Enol Ethers
Voegerl, Katharina
Ong, Duc Nghia
Bracher, Franz
SYNTHESIS-STUTTGART, 2018, 50 (06): : 1323 - 1330
[43] FLUORINATED IMINES AND HYDRAZONES
KRESPAN, CG
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01): : 42 - &
[44] Synthesis of endocyclic enol methyl ethers of 3-acylthiotetronic acids and their reactions with amines
Budnikova, MV
Rubinov, DB
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (10) : 1478 - 1485
[45] SYNTHESIS OF AZAHETEROCYCLES FROM FUNCTIONALIZED IMINES
DEKIMPE, N
STEVENS, C
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1992, 101 (07): : 569 - 578
[46] CHEMISTRY OF ENOL ETHERS
EFFENBER.F
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (05) : 295 - &
[47] A general synthesis of substituted indoles from cyclic enol ethers and enol lactones
Campos, KR
Woo, JCS
Lee, S
Tillyer, RD
ORGANIC LETTERS, 2004, 6 (01) : 79 - 82
[48] Ag-catalyzed asymmetric Mannich reactions of enol ethers with aryl, alkyl, alkenyl, and alkynyl imines
Josephsohn, NS
Snapper, ML
Hoveyda, AH
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3734 - 3735
[49] OXIDATION OF ENOL ETHERS
RAPP, RD
BOROWITZ, IJ
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (20): : 1202 - &
[50] Mannich Reaction of Imines and Silyl Enol Ethers Induced by Radical Cation Salts: Synthesis of β-Amino Ketones
Jia, Xiao-dong
Wang, Wen-juan
Huo, Cong-de
Quan, Zheng-jun
Ren, Yan
Wang, Xi-cun
SYNLETT, 2010, (19) : 2964 - 2968

← 1 2 3 4 5 →