Influence of hydroperoxides on the enantioselectivity of metal-catalyzed asymmetric Baeyer-Villiger oxidation and epoxidation with chiral ligands

被引：56
作者：
Bolm, C
Beckmann, O
Kühn, T
Palazzi, C
Adam, W
Rao, PB
Saha-Möller, CR
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 17期
关键词：
D O I：
10.1016/S0957-4166(01)00417-7
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Chiral hydroperoxides have a significant influence on the enantioselectivity of the metal-catalyzed asymmetric Baeyer-Villiger oxidation of cyclic ketones and the epoxidation of allylic alcohols, when chiral ligands are employed. If both the ligand and the hydroperoxide are enantiopure. the ligand determines the formation of the preferred product enantiomer in both reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2441 / 2446
页数：6
相关论文
共 32 条
[1]   Metal-template effect in the asymmetric Weitz-Scheffer epoxidation of α,ß-enones by an optically active hydroperoxide [J].
Adam, W ;
Rao, PB ;
Degen, HG ;
Saha-Möller, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5654-5655
[2]   Titanium-catalyzed, asymmetric sulfoxidation of alkyl aryl sulfides with optically active hydroperoxides [J].
Adam, W ;
Korb, MN ;
Roschmann, KJ ;
Saha-Möller, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3423-3428
[3]   KINETIC RESOLUTION OF CHIRAL ALPHA-HYDROPEROXY ESTERS BY HORSERADISH PEROXIDASE-CATALYZED ENANTIOSELECTIVE REDUCTION TO ALPHA-HYDROXY ESTERS [J].
ADAM, W ;
FELL, RT ;
HOCH, U ;
SAHAMOLLER, CR ;
SCHREIER, P .
TETRAHEDRON-ASYMMETRY, 1995, 6 (05) :1047-1050
[4]   The titanium-catalyzed, asymmetric epoxidation of allylic alcohols with optically active hydroperoxides in the presence of achiral diol ligands [J].
Adam, W ;
Korb, MN .
TETRAHEDRON-ASYMMETRY, 1997, 8 (07) :1131-1142
[5]   ENZYME-CATALYZED ASYMMETRIC-SYNTHESIS - KINETIC RESOLUTION OF RACEMIC HYDROPEROXIDES BY ENANTIOSELECTIVE REDUCTION TO ALCOHOLS WITH HORSERADISH-PEROXIDASE [J].
ADAM, W ;
HOCH, U ;
LAZARUS, M ;
SAHAMOLLER, CR ;
SCHREIER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) :11898-11901
[6]  
Aoki M, 2001, HELV CHIM ACTA, V84, P187, DOI 10.1002/1522-2675(20010131)84:1<187::AID-HLCA187>3.0.CO
[7]  
2-O
[8]  
Behrens C. H., 1983, ALDRICHIM ACTA, V16, P67
[9]   MECHANISM OF ACID-CATALYZED REARRANGEMENT OF TRIARYLMETHYL HYDROPEROXIDES [J].
BISSING, DE ;
MCEWEN, WE ;
MATUSZAK, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) :3824-&
[10]  
Bolm C, 1997, ADV CAT PROCESS, V2, P43
1234