A Novel Method for the Synthesis of N-Per(poly)fluoroalkanesulfonyl Amino Acids

Abstract

Treatment of disilyl ketene acetals with per(poly)fluoroalkanesulfonyl azides at 0 °C in acetonitrile afforded N-sulfonyl-protected α-amino acids in good yields. The method provided a novel and convenient access to N-sulfonyl-protected α-amino acids.

amino acids - amination - disilyl ketene acetals - fluoroalkanesulfonyl azides - sulfonyl-protected

References

<A NAME="RF00101SS-1A">1a</A> Begley DJ. J. Pharm. Pharmacol.  1996,  48:  136 

<A NAME="RF00101SS-1B">1b</A> Crommelin DJA. Storm G. Eur. J. Pharm. Sci.  1994,  2:  17 

<A NAME="RF00101SS-2A">2a</A> Deuthaler RO. Tetrahedron  1994,  50:  1539 

<A NAME="RF00101SS-2B">2b</A> Williams RM. Synthesis of Optically Active α-Amino Acids   Pergamon; Oxford: 1989. 

<A NAME="RF00101SS-3A">3a</A> Hutton CA. White JM. Tetrahedron Lett.  1997,  38:  1643 

<A NAME="RF00101SS-3B">3b</A> Plummer MS. Shahripour A. Kaltenbronn JS. Lunney EA. Steinbaugh BA. Hamby JM. Hamilton HW. Sawyer TK. Humblet C. Doherty AM. Taylor MD. Hingorani G. Batley BL. Rapundalo ST. J. Med. Chem.  1995,  38:  2893 

<A NAME="RF00101SS-4">4</A> Nouvet A. Lamatory F. Lazaara R. Tetrahedron Lett.  1998,  39:  2099 

<A NAME="RF00101SS-5A">5a</A> Seerden JPG. Scheeren HW. Tetrahedron. Lett.  1993,  34:  2669 

<A NAME="RF00101SS-5B">5b</A> Seerden JPG. Scholte R. Anita WA. Scheeren HW. Tetrahedron Lett.  1994,  35:  4419 

<A NAME="RF00101SS-6">6</A> Wagner H. Harms K. Koert U. Meder S. Boheim G. Angew. Chem., Int. Ed. Engl.  1996,  35:  2643 

<A NAME="RF00101SS-7A">7a</A> Hassan HM. El-Nawawy MA. Abdel-Wahb ZH. Shedid SAM. Indian J. Heterocyl. Chem.  1997,  7:  35 

<A NAME="RF00101SS-7B">7b</A> Gobeaux B. Ghosez L. Heterocycles  1989,  28:  29 

<A NAME="RF00101SS-8A">8a</A> Clark CR. Bouhadir K. Mayfield CA. DeRuiter J. J. Chromatogr. Sci.  1990,  407 

<A NAME="RF00101SS-8B">8b</A> DeRuiter J. Borne RF. Mayfield CA. J. Med. Chem.  1989,  141 

<A NAME="RF00101SS-9">9</A> Supuram CT. Briganti F. Mimcione G. Scozzafara A. J. Enzyme Inhib.  2000,  15:  111 

<A NAME="RF00101SS-10">10</A> Nakai S, and Sato H. inventors; (Toray Industries, Inc., Japan) Jpn. Kokai Tokkyo Koho JP 09124595 A2  09124595 A2 Heisei. 

<A NAME="RF00101SS-11">11</A> Yamamoto M, and Yoshida S. inventors; (CORPORATE SOURCE Nippon Chemiphar Co., Ltd, Japan) SOURCE PCT Int. Appl. WO 2000020403  WO 2000020403 A1. 

<A NAME="RF00101SS-12A">12a</A> Berry MB. Craieg D. Synlett  1992,  41 

<A NAME="RF00101SS-12B">12b</A> Mechesney EW. Swann WK. Jr. J. Am. Chem. Soc.  1937,  59:  1116 

<A NAME="RF00101SS-13">13</A> Xu Y. Xu GL. Zhu SZ. J. Fluorine Chem.  1999,  96:  79 

<A NAME="RF00101SS-14">14</A> Ainsworth C. Kuo YN. J. Organomet. Chem.  1972,  46:  73 

<A NAME="RF00101SS-15">15</A> Zhu SZ. J. Chem. Soc., Perkin Trans 1  1994,  2077 

<A NAME="RF00101SS-16">16</A> Xu Y. Zhu SZ. Tetrahedron  1999,  55:  13725 

<A NAME="RF00101SS-17">17</A> Stepan JF. Marcus E. J. Heterocycl. Chem.  1969,  6:  969 

<A NAME="RF00101SS-18">18</A> Cipollone A. Lorto MA. Pellacani L. Tardella PA. J. Org. Chem.  1987,  52:  2584