CHEMISTRY OF ETHYL 2-([TERT-BUTOXYCARBONYL(METHYL)AMINO]METHYL)-3-HYDROXY-3-PHENYL (OR 3-VINYL)PROPIONATE - MECHANISTIC CONSIDERATIONS IN THE FORMATION OF TETRAHYDRO-1,3-OXAZIN-2-ONES | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7905117

Reference Type

Journal Article

Title

CHEMISTRY OF ETHYL 2-([TERT-BUTOXYCARBONYL(METHYL)AMINO]METHYL)-3-HYDROXY-3-PHENYL (OR 3-VINYL)PROPIONATE - MECHANISTIC CONSIDERATIONS IN THE FORMATION OF TETRAHYDRO-1,3-OXAZIN-2-ONES

Author(s)

Kurihara, T; Matsubara, Y; Harusawa, S; Yoneda, R

Year

1991

Journal

Journal of the Chemical Society, Perkin Transactions 1
ISSN: 1472-7781
EISSN: 1364-5463

Issue

Page Numbers

3177-3183

Language

English

DOI

10.1039/p19910003177

Web of Science Id

WOS:A1991GV27900041

Abstract

The threo- and erythro-selective aldol condensation of ethyl 3-[t-butoxycarbonyl(methyl)amino]-propionate with benzaldehyde gave the benzylic alcohol-substituted aminopropionate ethyl 2-{[t-butoxycarbonyl(methyl)amino] methyl}-3-hydroxy-3-phenylpropionate as a diastereoisomeric mixture. On treatment with methanesulphonyl chloride and triethylamine, the threo-isomer was converted into ethyl 3-methyl-2-oxo-6-phenyl-3,4,5,6-tetrahydro-2H-1,3-oxazine- 5-carboxylate, and the erythro-isomer gave simply its corresponding mesate derivative. The mechanism for this transformation is discussed.