A chiral Lewis acid strategy for enantioselective allylic C-H oxidation

被引:226
作者
Covell, Dustin J. [1 ]
White, M. Christina [1 ]
机构
[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
关键词
allylic oxidation; C-H activation; enantioselectivity;
D O I
10.1002/anie.200802106
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Skip the chiral ligand: A chiral Lewis acid strategy for effecting asymmetric induction in oxidative systems not amenable to strongly binding chiral ligands is disclosed and its mechanism investigated. The highest levels of enantioselectivity for allylic C-H oxidation of terminal olefins is reported (see scheme; BQ=1,4-benzoquinone, LA*=chiral Lewis acid). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6448 / 6451
页数:4
相关论文
共 47 条
[1]  
Albéniz AC, 2001, CHEM-EUR J, V7, P2481, DOI 10.1002/1521-3765(20010601)7:11<2481::AID-CHEM24810>3.0.CO
[2]  
2-2
[3]   Copper catalyzed allylic oxidation with peresters [J].
Andrus, MB ;
Lashley, JC .
TETRAHEDRON, 2002, 58 (05) :845-866
[4]   Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate [J].
Andrus, MB ;
Zhou, ZN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8806-8807
[5]   THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE [J].
ANDRUS, MB ;
ARGADE, AB ;
CHEN, X ;
PAMMENT, MG .
TETRAHEDRON LETTERS, 1995, 36 (17) :2945-2948
[6]   EVIDENCE FOR (PI-ALLYL)PALLADIUM(II)(QUINONE) COMPLEXES IN THE PALLADIUM-CATALYZED 1,4-DIACETOXYLATION OF CONJUGATED DIENES [J].
BACKVALL, JE ;
GOGOLL, A .
TETRAHEDRON LETTERS, 1988, 29 (18) :2243-2246
[7]   A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics [J].
Brubaker, Jason D. ;
Myers, Andrew G. .
ORGANIC LETTERS, 2007, 9 (18) :3523-3525
[8]   A remarkable anion effect on the enantioselectivity of the Pd-catalyzed allylic amination using ferrocenyl ligands [J].
Burckhardt, U ;
Baumann, M ;
Togni, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :155-159
[9]   Serial ligand catalysis: A highly selective allylic C-H oxidation [J].
Chen, MS ;
Prabagaran, N ;
Labenz, NA ;
White, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6970-6971
[10]   A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation [J].
Chen, MS ;
White, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1346-1347