Enantioselective alkene radical cations reactions

被引：30

作者：

Crich, David ^{[1
]}

Shirai, Michio ^{[1
]}

Brebion, Franck ^{[1
]}

Rumthao, Sochanchingwung ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 27期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/j.tet.2006.03.063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of enantiomerically enriched 2-methyl-2-nitro-3-(diphenylphosphatoxy)alkyl radicals with tributyltin hydride and AlBN in benzene at reflux results in the formation of alkene radical cation/anion pairs. which are trapped intramolecularly by amine nucleophiles, leading to pyrrolidine and piperidine systems with memory of stereochemistry. The scope and limitations of the system are explored with respect to nucleophile, leaving group, and substituents within the substrate back-bone. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6501 / 6518

页数：18

共 59 条

[1] Synthesis of enantiopure 3-alkyl-perhydroazepines by diastereoselective 7-endo-radical cyclisation on a chiral 1,3-perhydrobenzoxazine derivative
Andrés, C
Duque-Soladana, JP
Iglesias, JM
Pedrosa, R
[J]. TETRAHEDRON LETTERS, 1999, 40 (12) : 2421 - 2424
[2] DYNAMICS OF INTERCONVERSION OF CONTACT AND SOLVENT-SEPARATED RADICAL-ION PAIRS
ARNOLD, BR
NOUKAKIS, D
FARID, S
GOODMAN, JL
GOULD, IR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) : 4399 - 4400
[3] Direct detection of ion pair formation and collapse in a migration reaction of a β-phosphate radical
Bagnol, L
Horner, JH
Newcomb, M
[J]. ORGANIC LETTERS, 2003, 5 (26) : 5055 - 5058
[4] Product studies and laser flash photolysis on alkyl radicals containing two different β-leaving groups are consonant with the formation of an olefin cation radical
Bales, BC
Horner, JH
Huang, XH
Newcomb, M
Crich, D
Greenberg, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) : 3623 - 3629
[5] Chemistry of β-(acyloxy)alkyl and β-(phosphatoxy)alkyl radicals and related species:: Radical and radical ionic migrations and fragmentations of carbon-oxygen bonds
Beckwith, ALJ
Crich, D
Duggan, PJ
Yao, QW
[J]. CHEMICAL REVIEWS, 1997, 97 (08) : 3273 - 3312
[6] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY
BECKWITH, ALJ
SCHIESSER, CH
[J]. TETRAHEDRON, 1985, 41 (19) : 3925 - 3941
[7] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS
BECKWITH, ALJ
[J]. TETRAHEDRON, 1981, 37 (18) : 3073 - 3100
[8] BELLTRAN A, 1985, B SOC CHIM FR, P491
[9] Thermal and catalyzed [3,3]-phosphorimidate rearrangements
Chen, B
Mapp, AK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (18) : 6712 - 6718
[10] Phosphorimidate rearrangement for the facile and selective preparation of allylic amines
Chen, B
Mapp, AK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) : 5364 - 5365

← 1 2 3 4 5 6 →