Cyclizations of aminyl radicals generated from substoichiometric stannane

Synlett

Volumn , Issue 20, 2010, Pages 3035-3038

  Zhai, Huimin ^a   Wickenden, Jason G ^a   Sammis, Glenn M ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

aminyl radical cyclization; cyclic imines; silyl enol ethers; substoichiometric tributyltin hydride

Indexed keywords

AZIDE; IMINE; PYRROLIDINE DERIVATIVE; TRIBUTYLTIN; TRIBUTYLTIN HYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; HYDROXYLATION; METHODOLOGY; PROCESS OPTIMIZATION; PROTON TRANSPORT; STOICHIOMETRY;

EID: 78650169718     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259062     Document Type: Article

References (19)

1. For reviews on nitrogen-centered radicals, see:, Neale [nl]R S., Synthesis 1971 1
2. Mackiewicz P, Furstoss R, Tetrahedron 1978 34 3241
3. Stella L, Angew. Chem., Int. Ed. Engl. 1983 22 337
4. Esker J L., Newcomb M, Adv. Heterocycl. Chem. 1993 58 1
5. Zard S Z., Synlett 1996 1148
6. Fallis A G., Brinza I M., Tetrahedron 1997 53 17543
7. Zard S Z., Chem. Soc. Rev. 2008 37 1603
8. Curran D P., In Comprehensive Organic Synthesis Vol. 4 Trost B M. Fleming I Pergamon Press Oxford 1991 811
9. Stella L, In Radicals in Organic Synthesis Vol. 2 Renaud P Sibi M P. Wiley-VCH Weinheim 2001 407
10. For initial studies, see:, Kim S, Joe G H., Do J Y., [nl]J. Am. Chem. Soc. 1993 115 3328
11. Kim S, Joe G H., Do J Y., J. Am. Chem. Soc. 1994 116 5521
12. Minozzi M, Nanni D, Spagnolo P, Chem. Eur. J. 2009 15 7830
13. Zhai H, Zlotorzynska M, Sammis G M., Chem. Commun. 2009 5716
14. For a review of radical hydrogen transfer reactions, see:, Robertson J, Pillai J, Lush R K., Chem. Soc. Rev. 2001 30 94
15. For representative examples of hydrogen abstraction to amines, see:, Routaboul L, Vanthuyne N, Gastaldi S, Gil G, Bertrand M, J. Org. Chem. 2008 73 364
16. ElBlidi L, Nechab M, Vanthuyne N, Gastildi S, Bertrand M, Gil G, J. Org. Chem. 2009 74 2901
17. Benati L, Bencivenni G, Leardini R, Nanni D, Minozzi M, Spagnolo P, Scialpi R, Zanardi G, Org. Lett. 2006 8 2499
18. Marco J L., J. Heterocycl. Chem. 1986 1059
19. Arai T, Abe H, Aoyagi S, Kibayashi C, Tetrahedron Lett. 2004 45 5921