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Communication | Regular issue | Vol 27, No. 3, 1988, pp.667-671
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4436
An Abnormal Reaction of N-tert-Butoxycarbonyl Group: Mechanistic Consideration for the Preparation of 2-Oxotetrahydro-1,3-oxazine

Yoshitaka Matsubara, Ryuji Yoneda, Shinya Harusawa, and Takushi Kurihara*

*Faculty of Pharmaceutical Science, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan


Threo- and erythro-selective aldol condensations of 3-aminopropionate (1) with benzaldehyde (2) gave β-hydroxy ester (3) as a mixture of diastersomers (threo/erythro: 79/21 and 26/74). Upon treatment with methanesulfonyl chloride and triethylamine, threo-3 was converted to 2-oxotetrahydro-1,3-oxazine (4) via mesylate, while erythro-3 gave the corresponding mesylate (5). A plausible mechanistic consideration is also described.