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Synthesis, asymmetric aldol reactions, and x-ray crystallography of some oxadiazinanone derivatives

✍ Scribed by Shawn R. Hitchcock; Ryan A. Davis; Daniel M. Richmond; Delvis D. Dore; Stephanie L. Kuschel; Jeremy F. Vaughn; Jesse A. Wolfe; Christopher G. Hamaker; David M. Casper; Jarvis Dingle

Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 633 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450502

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✦ Synopsis

A series of N 4 -substituted oxadiazinanones have been synthesized from (1R,2S)-norephedrine by a process of either reductive alkylation or arylation, N-nitrosation, reduction and cyclization. These derivatives (R = -CH 2 Ph, -CH 2 C(CH 3 ) 3 , -cyclo-C 6 H 11 , -C 6 H 5 ) have been acylated with propanoyl chloride and employed in the asymmetric Aldol reaction. The observed diastereoselectivities for the formation of the "non-Evans" syn-adduct ranged from 88:12 to 99:1. The hydrolysis of the Aldol adducts varied with the nature of the nitrogen substituent.

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