Allyl Silane Additions to Highly Electrophilic 5,6-Dihydro-2H-1,4- oxazinones

Cynthia   M.   Shafer; Julie      Pigza; Tadeusz   F.   Molinski

doi:10.2174/157017809787893046

Abstract

Allylsilane addition to the dihydro-2H-1,4-oxazinones, 1, proceeded in moderate to good yields with transdiastereoselectivity. The yield of addition reactions of 5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one with allylsilanes is improved over the corresponding additions of Grignard reagents to 1 and illustrates a simple path to protected β,β- disubstituted α-amino acids.

Keywords: Imine, amino acid, oxazinone, morpholinone

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Letters in Organic Chemistry

Title: Allyl Silane Additions to Highly Electrophilic 5,6-Dihydro-2H-1,4- oxazinones

Volume: 6 Issue: 3

Author(s): Cynthia M. Shafer, Julie Pigza and Tadeusz F. Molinski

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Keywords: Imine, amino acid, oxazinone, morpholinone

Abstract: Allylsilane addition to the dihydro-2H-1,4-oxazinones, 1, proceeded in moderate to good yields with transdiastereoselectivity. The yield of addition reactions of 5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one with allylsilanes is improved over the corresponding additions of Grignard reagents to 1 and illustrates a simple path to protected β,β- disubstituted α-amino acids.

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Shafer M. Cynthia, Pigza Julie and Molinski F. Tadeusz, Allyl Silane Additions to Highly Electrophilic 5,6-Dihydro-2H-1,4- oxazinones, Letters in Organic Chemistry 2009; 6 (3) . https://dx.doi.org/10.2174/157017809787893046