Regio- and enantioselective synthesis of allylic fluorides by electrophilic fluorodesilylation of allyl silanes

被引：108

作者：

Greedy, B

Paris, JM

Vidal, T

Gouverneur, V

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

[2] Rhodia Rech, Ctr Rech Lyon, F-69192 St Fons, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 28期

关键词：

allylic compounds; asymmetric synthesis; cinchona alkaloids; fluorides; silanes;

D O I：

10.1002/anie.200351405

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiopure N-fluorocinchona alkaloids promoted the electrophilic fluorodesilylation of allyl silanes in a conceptually new approach to the regio- and enantioselective formation of allylic fluorides (see scheme). Excellent conversions were observed in these reactions, which afforded the desired allylic fluorides with up to 96% ee.

引用

页码：3291 / 3294

页数：4

共 41 条

[1] Enantioselective electrophilic fluorination in ionic liquids
Baudequin, C
Plaquevent, JC
Audouard, C
Cahard, D
[J]. GREEN CHEMISTRY, 2002, 4 (06) : 584 - 586
[2] A NOVEL SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES AND GAMMA-FLUOROALKYLPHOSPHONATES
BLACKBURN, GM
KENT, DE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (11) : 511 - 513
[3] BROOK MA, 2000, SILICON ORGANIC ORGA, pCH14
[4] Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4)
Cahard, D
Audouard, C
Plaquevent, JC
Roques, N
[J]. ORGANIC LETTERS, 2000, 2 (23) : 3699 - 3701
[5] N-Fluorocinchonidinium tetrafluoroborate F-CD-BF4:: purification and structure elucidation of this novel enantioselective electrophilic fluorinating agent
Cahard, D
Audouard, C
Plaquevent, JC
Toupet, L
Roques, N
[J]. TETRAHEDRON LETTERS, 2001, 42 (10) : 1867 - 1869
[6] FLUORODEHYDROXYLATION OF ANTHRACYCLINONES WITH DAST SYNTHESIS OF 8-(S)-FLUORODAUNORUBICIN
CANFARINI, F
GIOLITTI, A
GUIDI, A
PASQUI, F
PESTELLINI, V
ARCAMONE, F
[J]. TETRAHEDRON LETTERS, 1993, 34 (29) : 4697 - 4700
[7] Asymmetric synthesis of 2-deoxy-2-fluoro-gamma-aldonolactones and their conversion to 2-deoxy-2-fluoropentoses
Davis, FA
Qi, HY
[J]. TETRAHEDRON LETTERS, 1996, 37 (25) : 4345 - 4348
[8] Gouverneur V, 2002, CHEM-EUR J, V8, P767
[9] The first enantiocontrolled synthesis of E,E conjugated dienes with a fluorine atom in the allylic position
Gree, DM
Kermarrec, CJM
Martelli, JT
Gree, RL
Lellouche, JP
Toupet, LJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) : 1918 - 1919
[10] Fluorodesilylation of alkenyltrimethylsilanes: a new route to fluoroalkenes and difluoromethyl-substituted amides, alcohols or ethers
Greedy, B
Gouverneur, V
[J]. CHEMICAL COMMUNICATIONS, 2001, (03) : 233 - 234

← 1 2 3 4 5 →