Synthesis 2005(15): 2549-2561  
DOI: 10.1055/s-2005-872122
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Single-Enantiomer 6-Hydroxy-7-phenyl-1,4-oxazepan-5-ones

Christopher W. Becker, Bruce T. Dembofsky, James E. Hall, Robert T. Jacobs, Don E. Pivonka, Cyrus J. Ohnmacht*
Department of Medicinal Chemistry, AstraZeneca Pharmaceuticals LP, PO Box 15437, Wilmington, DE 19850-5437, USA
Fax: +1(302)8864989; e-Mail: cyrus.ohnmacht@astrazeneca.com;
Further Information

Publication History

Received 18 January 2005
Publication Date:
04 August 2005 (online)

Abstract

An efficient two-step preparation of (6R,7R)-6-hydroxy-7-phenyl-1,4-oxazepan-5-ones (1) starting from aminoethanols and (2R,3S)-3-phenyloxirane-2-carboxylic ethyl ester or potassium salt has been described. The most efficient catalyst identified for the ring closure of the resulting intermediate epoxyamides was Sc(OTf)3. By choice of appropriate chiral starting substituted aminoethanol and 3-phenyloxirane-2-carboxylic derivatives, the procedure allows facile synthesis of other single enantiomer 6-hydroxy-7-phenyl-1,4-oxazepan-5-ones.

    References

  • 1 Karikomi M. Watanabe S. Kimura Y. Uyehara T. Tetrahedron Lett.  2002,  43:  1495 
  • 2 Righi G. Pescatore G. Bonadies F. Bonini C. Tetrahedron  2001,  57:  5649 
  • 3 Huang D.-F. Huang L. Tetrahedron  1990,  46:  3135 
  • 4 Baldwin JE. J. Chem. Soc., Chem. Commun.  1976,  734 
  • 5 Marson CM. McGregor J. Khan A. Grinter TJ. J. Org. Chem.  1998,  63:  7833 
  • 6 Baldas J. Porter QN. Aust. J. Chem.  1967,  20:  2655 ; Chem. Abstr. 1968, 68, 86666k
  • 8 Harada K. J. Org. Chem.  1966,  31:  1407 
  • 9 Thijs L. Porskamp JJM. van Loon AAWM. Derks MPW. Feenstra RW. Legters J. Zwanenburg B. Tetrahedron  1990,  46:  2611 
  • 10 Jacobsen EN. Deng L. Furukawa Y. Martinez LE. Tetrahedron  1994,  50:  4323 
  • 11 Kay JB. Robinson JB. J. Chem. Soc. C  1969,  248 
  • 12 Pracejus H. Pracejus G. Costisella B. J. Prakt. Chem.  1987,  329:  235 
  • 13 Lu X. Xu Z. Tang G. Org. Process Res. Dev.  2001,  5:  184 
  • 14 Bodurow CC. Boyer BD. Brennan J. Bunnell CA. Burks JE. Carr MA. Doecke CW. Eckrich TM. Fisher JW. Gardner JP. Graves BJ. Hines P. Hoying RC. Jackson BG. Kinnick MD. Kochert CD. Lewis JS. Luke WD. Moore LL. Morin JMJ. Nist RL. Prather DE. Sparks DL. Vladuchick WC. Tetrahedron Lett.  1989,  30:  2321 
  • 15 Schouteeten A. Christidis Y. Mattioda G. Brienne MJ. Jacques J. Bull. Soc. Chim. Belg.  1979,  88:  897 ; Chem. Abstr. 1980, 93, 72225
  • 16 Karim A. Mortreux A. Petit F. Buono G. Peiffer G. Siv C. J. Organomet. Chem.  1986,  317:  93 
  • 17 Ito Y. Amino Y. Nakatsuka M. Saegusa T. J. Am. Chem. Soc.  1983,  105:  1586 
  • 18 Gunderson KG. Shapiro MJ. Doti RA. Skiles JW. Tetrahedron: Asymmetry  1999,  10:  3263 
  • 19 Coote SJ. Davies SG. Middlemiss D. Naylor A. J. Chem. Soc., Perkin Trans. 1  1989,  2223 
  • 20 Lyle GG. J. Org. Chem.  1960,  25:  1779 
  • 21 Men’shikov GP. Borodina GM. J. Gen. Chem. U.S.S.R. (Engl. Transl.)  1947,  17:  1569 ; Chem. Abstr. 1948, 42, 2245a
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Manuscript in progress.