Efficient Synthesis of N-Protected Trisubstituted Oxazolidines from Ketones, Vinyl Ethers, and Fluoroalkanesulfonyl Azides in Mild Conditions

Ping He; Shizheng Zhu

doi:10.1055/s-2005-869967

PAPER

Efficient Synthesis of N-Protected Trisubstituted Oxazolidines from Ketones, Vinyl Ethers, and Fluoroalkanesulfonyl Azides in Mild Conditions

Ping He^a, Shizheng Zhu*^a,b
^a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: zhusz@mail.sioc.ac.cn;
^b College of Chemical Environment, South China Normal University, Guangzhou 510631, P. R. China

Abstract

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Abstract

A facile one-step method has been developed for the synthesis of 2,3,5-trisubstituted oxazolidines in moderate yields by the three-component reaction of ketones, vinyl ethers, and fluoroalkanesulfonyl azides at 0 °C within five minutes. This practical synthetic method provides a convenient and expeditious access to N-per(poly)fluoroalkanesulfonyl oxazolidines.

Key words

fluoroalkanesulfonyl azide - ketone - vinyl ether - oxazolidine - multi-component reactions

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References

<A NAME="RF02205SS-1">1</A> Anastasm PT. Warner JC. Green Chemistry: Theory and Practice Oxford University Press; Oxford: 1998.

<A NAME="RF02205SS-2">2</A> Domling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168

<A NAME="RF02205SS-3A">3a</A> Okuyama Y. Nakano H. Hongo H. Tetrahedron: Asymmetry 2000, 11: 1193

<A NAME="RF02205SS-3B">3b</A> Falorni M. Collu C. Conti S. Giacomelli G. Tetrahedron: Asymmetry 1996, 7: 293

<A NAME="RF02205SS-3C">3c</A> Joshi NN. Prasad PRK. J. Org. Chem. 1997, 62: 3770

<A NAME="RF02205SS-4A">4a</A> Wagner B. Gonzalez GI. Tran Hun Dau ME. Zhu J. Bioorg. Med. Chem. 1999, 7: 737

<A NAME="RF02205SS-4B">4b</A> Guerrier L. Royer J. Grierson DS. Husson HP. J. Am. Chem. Soc. 1983, 105: 7754

<A NAME="RF02205SS-5A">5a</A> Semenov VP. Khim. Geterotsikl. Soedin. 1976, 12: 1613

<A NAME="RF02205SS-5B">5b</A> Semenov VP. Stroiman IM. Ogloblin KA. Khim. Geterotsikl. Soedin 1977, 1: 27

<A NAME="RF02205SS-5C">5c</A> Semenov VP. Stroiman IM. Ozemaya SV. Ogloblin KA. Khim. Geterotsikl. Soedin. 1977, 3: 332

<A NAME="RF02205SS-6A">6a</A> Ramachandran PV. In Asymmetric Fluoroorganic Chemistry: Synthesis, Applications and Future Directions, ACS Symposium Series 746 American Chemical Society; Washington DC: 2000.

<A NAME="RF02205SS-6B">6b</A> Ojima I. McCarthy JR. Welch JT. In Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639 American Chemical Society; Washington DC: 1996.

<A NAME="RF02205SS-6C">6c</A> Kukhar’ VP. Soloshonok VA. In Fluorine-containing Amino Acids: Synthesis and Properties Wiley; New York: 1995.

<A NAME="RF02205SS-6D">6d</A> Welch JT. In Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456 American Chemical Society; Washington DC: 1991.

<A NAME="RF02205SS-6E">6e</A> Welth JT. Eswarakrishnan S. In Fluorine in Bioorganic Chemistry Wiley-Interscience John Wiley & Sons; New York: 1991.

<A NAME="RF02205SS-7A">7a</A> Young JA. Simmons TC. Hoffmann FN. J. Am. Chem. Soc. 1956, 78: 5637

<A NAME="RF02205SS-7B">7b</A> Middleton WJ. Krespan CG. J. Org. Chem. 1967, 32: 951

<A NAME="RF02205SS-7C">7c</A> O’Brien BA. Lam WY. DesMarteau DD. J. Org. Chem. 1986, 51: 4466

<A NAME="RF02205SS-8">8</A> Gosselin F. Roy A. O’Shea PD. Chen CY. Volante RP. Org. Lett. 2004, 6: 641

<A NAME="RF02205SS-9A">9a</A> Xu Y. Wang YL. Zhu SZ. J. Fluorine Chem. 2000, 104: 195

<A NAME="RF02205SS-9B">9b</A> Xu Y. Zhu SZ. Tetrahedron 2001, 57: 669

<A NAME="RF02205SS-9C">9c</A> Zhu SZ. Jin GF. Zhao JW. J. Fluorine Chem. 2003, 120: 65

<A NAME="RF02205SS-10">10</A> Zhu SZ. He P. Zhao JW. Cai X. J. Fluorine Chem. 2004, 125: 445

<A NAME="RF02205SS-11">11</A> Weuthen M. Scharf HD. Runsink J. Chem. Ber. 1987, 120: 1023

He, P.; Zhu, S. Z. Tetrahedron 2005, in press.

CCDC number: CCDC 262795

<A NAME="RF02205SS-14">14</A> Wang LJ. Seiders JR. Floreancig PE. J. Am. Chem. Soc. 2004, 126: 12596

<A NAME="RF02205SS-15">15</A> Zhu SZ. Tetrahedron Lett. 1992, 33: 6503