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Synthesis 2015; 47(10): 1488-1498
DOI: 10.1055/s-0034-1380163
DOI: 10.1055/s-0034-1380163
paper
A Mild Protocol for the Regioselective Ring Opening of Doubly Activated Cyclopropanes by Using Selenolates Generated in Situ: Synthesis of Functionalized Organoselenium Compounds
Authors
Further Information
Publication History
Received: 02 August 2014
Accepted after revision: 21 January 2015
Publication Date:
27 February 2015 (online)
Abstract
A variety of functionalized organoselenium compounds were synthesized from doubly activated cyclopropanes and diselenides in the presence of sodium borohydride. A range of substituents were stable under these reaction conditions. Additionally, we extended the scope of the method by reducing nitro groups in the products to give the corresponding selenium-containing unnatural amino acids.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380163.
- Supporting Information (PDF)
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References
- 1 Holben DH, Smith AM. J. Am. Diet. Assoc. 1999; 99: 836
- 2a Klayman DL, Griffin TS. J. Am. Chem. Soc. 1973; 95: 197
- 2b Gladysz JA, Hornby JL, Garbe JE. J. Org. Chem. 1978; 43: 1204
- 2c Thomson DP, Boudjouk P. J. Org. Chem. 1988; 53: 2109
- 2d Copeland CM, Ghosh J, McAdam DP, Skelton BW, Stick RV, White AH. Aust. J. Chem. 1988; 41: 549
- 2e Li GM, Zingaro RA. J. Chem. Soc., Perkin Trans. 1 1998; 647
- 2f Ishihara H, Koketsu M, Fukuta Y, Nada F. J. Am. Chem. Soc. 2001; 123: 8408
- 2g Perin G, Lenardão EJ, Jacob RG, Panatieri RB. Chem. Rev. 2009; 109: 1277
- 2h Piovan L, Alves MF. M, Juliano L, Brömme D, Cunha RL. O. R, Andrade LH. J. Braz. Chem. Soc. 2010; 21: 2108
- 2i Hua G, Fuller AL, Slawin AM. Z, Woolins JD. Polyhedron 2011; 30: 805
- 2j Frizon TE, Rampon DS, Gallardo H, Merlo AA, Schneider PH, Rodrigues OE. D, Braga AL. Liq. Cryst. 2012; 39: 769
- 3a Stewart JM, Westberg HH. J. Org. Chem. 1965; 30: 1951
- 3b Corey EJ, Fuchs PL. J. Am. Chem. Soc. 1972; 94: 4014
- 3c Danishefsky S. Acc. Chem. Res. 1979; 12: 66
- 3d Miller RD, McKean DR. J. Org. Chem. 1981; 46: 2412 ; and references therein
- 3e Blanchard LA, Schneider JA. J. Org. Chem. 1986; 51: 1372
- 3f Seebach D, Häner R, Vettiger T. Helv. Chim. Acta 1987; 70: 1507
- 3g Wurz RP, Charette AB. Org. Lett. 2005; 7: 2313
- 3h Budynina EM, Ivanova OA, Avertina EB, Kuznetsova TS, Zefirov NS. Tetrahedron Lett. 2006; 47: 647
- 3i Lifchits O, Alberico D, Zakharian I, Charette AB. J. Org. Chem. 2008; 73: 6838
- 3j Lifchits O, Charette AB. Org. Lett. 2008; 10: 2809
- 3k Lebold TP, Kerr MA. Org. Lett. 2009; 11: 4354
- 4a Kocienski P, Yeates C. J. Chem. Soc., Perkin Trans. 1 1985; 1879
- 4b Krief A, Trabelsi M. Tetrahedron Lett. 1987; 28: 4225
- 4c Krief A, Trabelsi M. Synth. Commun. 1989; 19: 1203
- 4d Natsuko K, Ihara M, Toyota M. Org. Lett. 2006; 8: 875
- 4e Yang S.-H, Clark GR, Caprio V. Org. Biomol. Chem. 2009; 7: 2981
- 4f Xu J, Wu L, Huang X. J. Org. Chem. 2011; 76: 5598
- 5 Gopinath P, Chandrasekaran S. J. Org. Chem. 2011; 76: 700
- 6 Prabhu KR, Devan N, Chandrasekaran S. Synlett 2002; 1762
- 7 The ring opening of singly activated cyclopropanes and alkyl-substituted cyclopropanes is not very efficient.
- 8 Krief A, Delmotte C, Dumont W. Tetrahedron Lett. 1997; 38: 3079
- 9 Wurz RP, Charette AB. Org. Lett. 2003; 5: 2327
- 10 Commercial-grade solvents were distilled and dried according to literature procedures, see: Perrin DD, Armarego WL. F. Purification of Laboratory Chemicals . 3rd ed Butterworth-Heinemann; Oxford: 1988
- 11 Heiszman J, Bitter I, Harsányi K, Töke L. Synthesis 1987; 738
- 12 Biland AS, Altermann S, Wirth T. ARKIVOC 2003; (vi): 164
- 13 Zhang Y, Jia X, Zhou X. Synth. Commun. 1994; 24: 1247
- 14 Syper L, Mlochowski J. Tetrahedron 1988; 44: 6119
- 15 Gautheron B, Tainturier G, Degrand C. J. Am. Chem. Soc. 1985; 107: 5579