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

被引：259

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 41期

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

页码：15342 / 15345

页数：4

共 27 条

[1] Synthesis and evaluation of a broad range of chiral sulfides for asymmetric sulfur ylide epoxidation of aldehydes
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
[J]. 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
ARNAUD, R
POSTLETHWAITE, H
BARONE, V
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (23) : 5913 - 5919
[3] FORMATION OF QUATERNARY CARBON CENTERS FROM TERTIARY ALCOHOLS BY FREE-RADICAL METHODS
BARTON, DHR
CRICH, D
[J]. 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
BARTON, DHR
CRICH, D
KRETZSCHMAR, G
[J]. 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
BARTON, DHR
SAS, W
[J]. 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
Beckwith, ALJ
Poole, JS
[J]. 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
Blazejewski, JC
Diter, P
Warchol, T
Wakselman, C
[J]. 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
DAMM, W
GIESE, B
HARTUNG, J
HASSKERL, T
HOUK, KN
ZIPSE, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) : 4067 - 4079
[10] Total Synthesis of (+)-Gliocladin C Enabled by Visible-Light Photoredox Catalysis
Furst, Laura
Narayanam, Jagan M. R.
Stephenson, Corey R. J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (41) : 9655 - 9659

← 1 2 3 →