Diastereoselective Allylstannane Additions to ( S )-5,6-Dihydro-2 H -5-phenyloxazin-2-one. A Concise Synthesis of ( S )-β-Methylisoleucine

The addition of allyl stannanes to ( S )-4,5-dihydro-5-phenyl-2 H -oxazinone (3) was achieved under Brønsted acid catalysistogive 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1).The product of dimethylallyltributylstannane addition to 3 was converted to L-β-methylisoleucine, an...

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Bibliographic Details
Published in:Organic letters 2010-03, Vol.12 (6), p.1256-1259
Main Authors: Pigza, Julie A., Molinski, Tadeusz F.
Format: Article
Language:English
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Summary:The addition of allyl stannanes to ( S )-4,5-dihydro-5-phenyl-2 H -oxazinone (3) was achieved under Brønsted acid catalysistogive 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1).The product of dimethylallyltributylstannane addition to 3 was converted to L-β-methylisoleucine, an α-amino acid residue found in the complex, biologically-active marine-derived peptides polytheonamides A and B and polydiscamides A–C.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1001126