Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents

被引：70
作者：
Brown, Michael [1 ]
Kumar, Ravi [1 ]
Rehbein, Julia [2 ]
Wirth, Thomas [1 ]
机构：
[1] Cardiff Univ, Sch Chem, Pk Pl,Main Bldg, Cardiff CF10 3AT, S Glam, Wales
[2] Univ Hamburg, Organ Chem, Martin Luther King Pl 6, D-20146 Hamburg, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 12期
基金：
英国工程与自然科学研究理事会;
关键词：
alkenes; arylation; hypervalent iodine; oxidation; rearrangement; CATALYZED ALPHA-ARYLATION; CROSS-COUPLINGS; BOND ACTIVATION; PALLADIUM; KETONES; ALKENES; SPIROLACTONIZATION; FUNCTIONALIZATION; CYCLOOXYGENASE-2; THERMOCHEMISTRY;
D O I：
10.1002/chem.201504844
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A stereoselective hypervalent iodine-promoted oxidative rearrangement of 1,1-disubstituted alkenes has been developed. This practically simple protocol provides access to enantioenriched -arylated ketones without the use of transition metals from readily accessible alkenes.
引用
收藏
页码：4030 / 4035
页数：6
相关论文
共 88 条
[1]   Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III) [J].
Ahmad, Anees ;
Scarassati, Paulo ;
Jalalian, Nazli ;
Olofsson, Berit ;
Silva, Luiz F., Jr. .
TETRAHEDRON LETTERS, 2013, 54 (43) :5818-5820
[2]   Asymmetric arylation of ketone enolates [J].
Ahman, J ;
Wolfe, JP ;
Troutman, MV ;
Palucki, M ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919
[3]   Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4260-4263
[4]  
[Anonymous], 2013, ANGEW CHEM, DOI DOI 10.1002/ANGE.201302358
[5]  
[Anonymous], 1997, ANGEW CHEM INT ED EN
[6]  
[Anonymous], 2010, ANGEW CHEM INT ED, DOI DOI 10.1002/ANGE.200907352
[7]  
Bartzatt Ronald, 2014, Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry, V13, P17
[8]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[9]   DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].
BECKE, AD .
PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100
[10]   Reagent and Catalyst Design for Asymmetric Hypervalent Iodine Oxidations [J].
Berthiol, Florian .
SYNTHESIS-STUTTGART, 2015, 47 (05) :587-603
123456789