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Synthesis 2012; 44(20): 3202-3208
DOI: 10.1055/s-0032-1316768
DOI: 10.1055/s-0032-1316768
paper
BF3·OEt2/TMSN3 Mediated Regioselective Azidolysis of Vinylaziridines
Further Information
Publication History
Received: 13 March 2012
Accepted after revision: 20 July 2012
Publication Date:
31 August 2012 (online)
Abstract
An easy and general azidolysis of vinylepoxides mediated by BF3·OEt2 and TMSN3 recently reported by our group has been extended to vinylaziridines. The reaction affords unsaturated azido derivatives with complete stereoselectivity and regioselectivity, when in the presence of electron-poor olefins, regardless of the size of substituents on the heterocyclic ring.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Current position: Dr. Ilaria Tirotta, Post Doctoral Researcher, Ludwig Maximilians-Universität München, Department Chemie & Biochemie, Butenandtstrasse 5-13, Haus F, 81377 München, Germany. Fax: +49(89)218077680
- 2a Olofsson B, Somfai P In Aziridines and Epoxides in Organic Synthesis . Yudin AK. Wiley-VCH; Weinheim: 2006: 315-443
- 2b Padwa A, Murphree SS. ARKIVOC 2006; (iii): 6
- 3 Ko SY, Lee AW. M, Masamune S, Reed L, Hi A, Sharpless KB, Walker FJ. Tetrahedron 1990; 46: 245
- 4 Righi G, Salvati Manni L, Bovicelli P, Pelagalli R. Tetrahedron Lett. 2011; 52: 3895
- 5a Rodrigues JA. R, Milagre H, Milagre CD. F, Moran PJ. S. Tetrahedron: Asymmetry 2005; 16: 3099
- 5b Ghorai MK, Kumar A, Tiwari DP. J. Org. Chem. 2010; 75: 137
- 5c Padwa A In Comprehensive Heterocyclic Chemistry III . Vol. 1. Padwa A. Elsevier; Oxford: 2008. Chap. 1.01
- 5d Fontana F, Chen CC, Aggarwal VK. Org. Lett. 2011; 13: 3454 ; and references cited therein
- 6a Miyashita M, Mizutani T, Tadano G, Iwata Y, Miyazawa M, Tanino K. Angew. Chem. Int. Ed. 2005; 44: 5094
- 6b Marié JC, Courillon C, Malacria M. ARKIVOC 2007; (v): 277
- 7 Solladié-Cavallo A, Lupattelli P, Bonini C. J. Org. Chem. 2005; 70: 1605
- 8 For the purpose of this work, it is not mandatory to have optically active compounds; all the molecules are intended as racemates and the reported stereochemistry is only relative.
- 9 For the substrates with R = cyclohexyl, the appropriate alcohol 1b is not commercially available and was synthesised from cyclohexanecarboxaldehyde. A Horner–Emmons reaction, followed by reduction of the resulting ester using DIBAL-H, led to alcohol 1b in an overall yield of 97%.
- 10a Antonioletti R, Bonadies F, Ciammaichella A, Viglianti A. Tetrahedron 2008; 64: 4644
- 10b Lattanzi A, Orelli LR, Barone P, Massa A, Iannece C, Scettri A. Tetrahedron Lett. 2003; 44: 1333
- 10c Bonadies F, Scettri A, Di Campli C. Tetrahedron Lett. 1996; 37: 1899
- 11 Legters J, Thijs L, Zwanemburg B. Recl. Trav. Chim. Pays-Bas 1992; 111: 1
- 12 Gao Y, Klunder JM, Hanson RM, Masamune H, Ko SY, Sharpless KB. J. Am. Chem. Soc. 1987; 109: 5765
- 13 De Mico A, Margarita R, Parlanti L, Vescovi A, Piancatelli G. J. Org. Chem. 1997; 62: 6974
- 14 Righi G, Chionne A, Bonini C. Eur. J. Org. Chem. 2000; 3127
- 15 Righi G, Bovicelli P, Barontini M, Tirotta I. Green Chem. 2012; 14: 495
- 16 Righi G, Mandic’ E, Naponiello GC. M, Bovicelli P, Tirotta I. Tetrahedron 2012; 68: 2984
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