Direct Construction of Quaternary Carbons from Tertiary Alcohols via Photoredox-Catalyzed Fragmentation of tert-Alkyl N-Phthalimidoyl Oxalates

被引:270
作者
Lackner, Gregory L. [1 ]
Quasdorf, Kyle W. [1 ]
Overman, Larry E. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
基金
美国国家科学基金会;
关键词
RADICAL REACTIONS; ADDITIONS; LIGHT; DERIVATIVES; XANTHATES; INVENTION; ALKENES; BONDS;
D O I
10.1021/ja408971t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convenient method for the direct construction of quaternary carbons from tertiary alcohols by visible-light photoredox coupling of tert-alkyl N-phthalimidoyl oxalate intermediates with electron-deficient alkenes is reported.
引用
收藏
页码:15342 / 15345
页数:4
相关论文
共 27 条
[1]   Synthesis and evaluation of a broad range of chiral sulfides for asymmetric sulfur ylide epoxidation of aldehydes [J].
Aggarwal, VK ;
Angelaud, R ;
Bihan, D ;
Blackburn, P ;
Fieldhouse, R ;
Fonquerna, SJ ;
Ford, GD ;
Hynd, G ;
Jones, E ;
Jones, RVH ;
Jubault, P ;
Palmer, MJ ;
Ratcliffe, PD ;
Adams, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (20) :2604-2622
[2]   THEORETICAL-STUDY OF THE ADDITION OF TERT-BUTYL AND BENZYL RADICALS TO ETHENE [J].
ARNAUD, R ;
POSTLETHWAITE, H ;
BARONE, V .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (23) :5913-5919
[3]   FORMATION OF QUATERNARY CARBON CENTERS FROM TERTIARY ALCOHOLS BY FREE-RADICAL METHODS [J].
BARTON, DHR ;
CRICH, D .
TETRAHEDRON LETTERS, 1985, 26 (06) :757-760
[4]   THE INVENTION OF NEW RADICAL CHAIN-REACTIONS .9. FURTHER RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - FORMATION OF CARBON CARBON BONDS [J].
BARTON, DHR ;
CRICH, D ;
KRETZSCHMAR, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (01) :39-53
[5]   THE INVENTION OF RADICAL REACTIONS .19. THE SYNTHESIS OF VERY HINDERED QUINONES [J].
BARTON, DHR ;
SAS, W .
TETRAHEDRON, 1990, 46 (10) :3419-3430
[6]   Factors affecting the rates of addition of free radicals to alkenes-determination of absolute rate coefficients using the persistent aminoxyl method [J].
Beckwith, ALJ ;
Poole, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9489-9497
[7]   Radical allylation of trifluoromethylated xanthates: use of DEAD for removing the allyltributyltin excess [J].
Blazejewski, JC ;
Diter, P ;
Warchol, T ;
Wakselman, C .
TETRAHEDRON LETTERS, 2001, 42 (05) :859-861
[8]  
Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858
[9]   DIASTEREOFACIAL SELECTIVITY IN REACTIONS OF SUBSTITUTED CYCLOHEXYL RADICALS - AN EXPERIMENTAL AND THEORETICAL-STUDY [J].
DAMM, W ;
GIESE, B ;
HARTUNG, J ;
HASSKERL, T ;
HOUK, KN ;
ZIPSE, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4067-4079
[10]   Total Synthesis of (+)-Gliocladin C Enabled by Visible-Light Photoredox Catalysis [J].
Furst, Laura ;
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (41) :9655-9659