Axially chiral NHC-Pd(II) complexes in the oxidative kinetic resolution of secondary alcohols using molecular oxygen as a terminal oxidant

被引:96
作者
Chen, Tao
Jiang, Jia-Jun
Xu, Qin
Shi, Min
机构
[1] E China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ol063061w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Axially chiral N-heterocyclic carbene (NHC) Pd(II) complexes were prepared from optically active 1,1'-binaphthalenyl-2,2'-diamine (BINAM) and H-8-BINAM and applied in the oxidative kinetic resolution of secondary alcohols using molecular oxygen as a terminal oxidant. The corresponding sec-alcohols can be obtained in good yields with moderate to good enantioselectivities.
引用
收藏
页码:865 / 868
页数:4
相关论文
共 38 条
[1]  
[Anonymous], 1990, OXIDATIONS ORGANIC C
[2]   Palladium-catalyzed oxidative kinetic resolution with ambient air as the stoichiometric oxidation gas [J].
Bagdanoff, JT ;
Stoltz, BM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (03) :353-357
[3]   Palladium-catalyzed enantioselective oxidation of alcohols:: A dramatic rate acceleration by Cs2CO3/t-BuOH [J].
Bagdanoff, JT ;
Ferreira, EM ;
Stoltz, BM .
ORGANIC LETTERS, 2003, 5 (06) :835-837
[4]   Carbamoyl-substituted N-heterocyclic carbene complexes of palladium(II):: Application to Sonogashira cross-coupling reactions [J].
Batey, RA ;
Shen, M ;
Lough, AJ .
ORGANIC LETTERS, 2002, 4 (09) :1411-1414
[5]   HOMOGENEOUS CATALYTIC-OXIDATION OF SECONDARY ALCOHOLS TO KETONES BY MOLECULAR-OXYGEN UNDER MILD CONDITIONS [J].
BLACKBURN, TF ;
SCHWARTZ, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (05) :157-158
[6]   Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].
César, V ;
Bellemin-Laponnaz, S ;
Gade, LH .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636
[7]  
CHULTZ MJ, 2002, CHEM COMMUN, P3034
[8]   Synthesis of novel axially chiral Rh-NHC complexes derived from BINAM and application in the enantioselective hydrosilylation of methyl ketones [J].
Duan, WL ;
Shi, M ;
Rong, GB .
CHEMICAL COMMUNICATIONS, 2003, (23) :2916-2917
[9]   The palladiuim-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen [J].
Ferreira, EM ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7725-7726
[10]  
Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO