Diastereoselective allylstannane additions to (S)-5,6-dihydro-2H-5-phenyloxazin-2-one. A concise synthesis of (S)-beta-methylisoleucine

Org Lett. 2010 Mar 19;12(6):1256-9. doi: 10.1021/ol1001126.

Abstract

The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2H-oxazinone (3) was achieved under Brønsted acid catalysis to give 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1). The product of dimethylallyltributylstannane addition to 3 was converted to l-beta-methylisoleucine, an alpha-amino acid residue found in the complex, biologically active marine-derived peptides polytheonamides A and B, and polydiscamides A-C.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Isoleucine / analogs & derivatives*
  • Isoleucine / chemical synthesis
  • Isoleucine / chemistry
  • Molecular Structure
  • Oxazines / chemistry*
  • Receptors, G-Protein-Coupled / antagonists & inhibitors
  • Stereoisomerism
  • Tin Compounds / chemistry*

Substances

  • 5,6-dihydro-2H-5-phenyloxazin-2-one
  • Oxazines
  • Receptors, G-Protein-Coupled
  • Tin Compounds
  • beta-methylisoleucine
  • Isoleucine
  • stannane