Diastereoselective allylstannane additions to (S)-5,6-dihydro-2H-5-phenyloxazin-2-one. A concise synthesis of (S)-beta-methylisoleucine.
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.
Pigza
Julie A
JA
Department of Chemistry and Biochemistry, and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, 9500 Gilman Drive MC0358, La Jolla, California 92093, USA.
Molinski
Tadeusz F
TF
D007532:Isoleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D043562:Receptors, G-Protein-Coupled / Q000037:antagonists & inhibitors; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*
C549993:5,6-dihydro-2H-5-phenyloxazin-2-one; D010078:Oxazines; D043562:Receptors, G-Protein-Coupled; D017971:Tin Compounds; C549994:beta-methylisoleucine; D007532:Isoleucine; C031525:stannane