A facile tandem reaction to access β-hydroxy-α,α-difluoroketone derivatives catalyzed by titanocene dichloride/magnesium

被引：5

作者：

Wu, Lei ^{[1
]}

机构：

[1] Harbin Inst Technol, Acad Fundamental & Interdisciplinary Sci, Harbin 150080, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2011年 / 132卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Tandem reaction; Barbier-type allylation; Brook rearrangement; Fluoride-promoted aldol reaction; ENOL SILYL ETHERS; ALDOL REACTIONS; ACYLSILANES; KETONES; TRIFLUOROMETHYLTRIMETHYLSILANE; HYDROGENATION; ALLYLATION; CHEMISTRY; SILANES; ACIDS;

D O I：

10.1016/j.jfluchem.2011.03.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Tandem reactions of Barbier-type allylation, Brook rearrangement and fluoride-promoted aldol reaction were developed, which afforded a facile, "one-pot" process to beta-hydroxy-alpha,alpha-difluoroketone derivatives with good to excellent yields. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：367 / 372

页数：6

共 33 条

[1] Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations
Ajamian, A
Gleason, JL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) : 3754 - 3760
[2] [Anonymous], 1999, COMPREHENSIVE ASYMME
[3] BEGUE JP, 1995, SYNLETT, P659
[4] REACTIONS OF SILYL AND GERMYL KETONES WITH ALKYLIDENEPHOSPHORANES
BROOK, AG
FIELDHOUSE, SA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 10 (02) : 235 - +
[5] Titanocene(III) Chloride-Mediated Reductions of Oxazines, Hydroxamic Acids, and N-Hydroxy Carbamates
Cesario, Cara
Tardibono, Lawrence P., Jr.
Miller, Marvin J.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) : 448 - 451
[6] Tandem and domino catalytic strategies for enantioselective synthesis
Chapman, Christopher J.
Frost, Christopher G.
[J]. SYNTHESIS-STUTTGART, 2007, (01): : 1 - 21
[7] A general method for synthesis of trifluoroacetyltrialkyl(aryl)silanes and the Sakurai reaction of fluorinated acylsilanes with allyl silanes
Chung, WJ
Welch, JT
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (04) : 543 - 548
[8] A HIGHLY EFFICIENT ADDITION OF ALLYLIC BROMIDES TO CARBONYL-COMPOUNDS PROMOTED BY CP2TICL2(CAT)/ZN SYSTEM
DING, Y
ZHAO, G
[J]. TETRAHEDRON LETTERS, 1992, 33 (52) : 8117 - 8118
[9] Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones
Evans, DA
Tedrow, JS
Shaw, JT
Downey, CW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) : 392 - 393
[10] The reduction of α-silyloxy ketones using phenyldimethylsilyllithium
Fleming, I
Roberts, RS
Smith, SC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (07): : 1215 - 1228

← 1 2 3 4 →