Bismuth Triflate as Novel and Efficient Catalyst for the Synthesis of β-Aminosulfides

Jhillu S. Yadav; B. V. Subba Reddy; Gakul Baishya; P. Venkatram Reddy; S. J. Harshavardhan

doi:10.1055/s-2004-829144

PAPER

Bismuth Triflate as Novel and Efficient Catalyst for the Synthesis of β-Aminosulfides

Jhillu S. Yadav*, B. V. Subba Reddy, Gakul Baishya, P. Venkatram Reddy, S. J. Harshavardhan
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in, yadavpub@iict.res.in;

Abstract

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Abstract

Aziridines undergo ring opening readily with various thiols in the presence of 5 mol% bismuth triflate under very mild reaction conditions to afford the corresponding β-aminosulfides in excellent yields with high regioselectivity.

Key words

aziridines - metal triflates - thiols - β-aminosulfides

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References

<A NAME="RZ02804SS-1A">1a</A> Katritzky AR. Rees CW. Comprehensive Heterocyclic Chemistry Vol. 7: Pergamon Press; Oxford: 1984. p.47

<A NAME="RZ02804SS-1B">1b</A> Kump JEG. Comprehensive Organic Synthesis Vol. 7: Trost BM. Fleming I. Pergamon Press; Oxford: 1991. p.469

<A NAME="RZ02804SS-2A">2a</A> Tanner D. Angew. Chem., Int. Ed. Engl. 1994, 33: 599

<A NAME="RZ02804SS-2B">2b</A> McCoull W. Davis FA. Synthesis 2000, 1347

<A NAME="RZ02804SS-3A">3a</A> Dureault A. Tranchepain I. Depezay JC. J. Org. Chem. 1989, 54: 5324

<A NAME="RZ02804SS-3B">3b</A> Tanner D. He HM. Tetrahedron 1992, 48: 6079

<A NAME="RZ02804SS-4">4</A> Hudlicky T. Luna H. Price JD. Rulin F. J. Org. Chem. 1990, 55: 4683

<A NAME="RZ02804SS-5A">5a</A> Bae JH. Shin SH. Park CS. Lee WK. Tetrahedron 1999, 55: 10041

<A NAME="RZ02804SS-5B">5b</A> Ingenitio R. Bianchi E. Fattori D. Pessi A. J. Am. Chem. Soc. 1999, 121: 11369

<A NAME="RZ02804SS-5C">5c</A> Adams B. Beresford KJM. Whyte SM. Young DW. J. Chem. Soc., Chem. Commun. 2000, 619

<A NAME="RZ02804SS-6A">6a</A> Carreaux F. Dureault A. Depezay JC. Synlett 1992, 527

<A NAME="RZ02804SS-6B">6b</A> Maligres PE. See MM. Askin D. Reider PJ. Tetrahedron Lett. 1997, 38: 5253

<A NAME="RZ02804SS-7A">7a</A> Wu J. Hou XL. Dai LX. J. Chem. Soc., Perkin Trans. 1 2001, 1314

<A NAME="RZ02804SS-7B">7b</A> Katagiri T. Takahashi M. Fujiwara Y. Ihara H. Uneyama K. J. Org. Chem. 1999, 64: 7323

<A NAME="RZ02804SS-7C">7c</A> Antolini L. Bucciarelli M. Caselli E. Davoli P. Forni A. Moretti I. Prati F. Torre G. J. Org. Chem. 1997, 62: 8784

<A NAME="RZ02804SS-8A">8a</A> Imamoto T. Lanthanides in Organic Synthesis Academic Press; London: 1994.

<A NAME="RZ02804SS-8B">8b</A> Molander GA. Chem. Rev. 1992, 92: 29

<A NAME="RZ02804SS-9A">9a</A> Kobayashi S. Synlett 1994, 689

<A NAME="RZ02804SS-9B">9b</A> Kobayashi S. J. Synth. Org. Chem., Jpn. 1995, 53: 370

<A NAME="RZ02804SS-9C">9c</A> Kobayashi S. Eur. J. Org. Chem. 1999, 15

<A NAME="RZ02804SS-10">10</A> Leonard MN. Wieland LC. Mohan RS. Tetrahedron 2002, 58: 8373

<A NAME="RZ02804SS-11">11</A> Repichet S. Zwick A. Vendier L. Le Roux C. Dubac J. Tetrahedron Lett. 2002, 43: 993