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Preparation, and nucleophilic addition-reactions, of 1,5- anhydro-4,6-O-benzylidene-2,3-dideoxy-2-nitro-d-erythro-hex-2-enitol

✍ Scribed by Tohru Sakakibara; Toshiaki Minami; Yoshiharu Ishido; Rokuro Sudoh

Publisher: Elsevier Science
Year: 1982
Tongue: English
Weight: 820 KB
Volume: 109
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(82)84037-8

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✦ Synopsis

Nucleophilic

addition-reactions of the title compound, prepared from the corresponding 3-nitrohex-2-enitol, were investigated under kinetically controlled conditions; such sterically bulky nucleophiles as tert-butyl peroxide and 2,4-pentanedionate ions (except in 1,Cdioxane)

were found to engage almost exclusively in equatorial attack, whereas, for hydroperoxide and deuteride ions, axial attack is favored. All the products thus obtained, other than the nitro epoxides, were subjected to an equilibration test. Factors potentially controlling the addition reactions under thermodynamically, as well as kinetically, controlled conditions are discussed, based on the results described herein. *Stereochemistry of Nucleophilic Addition Reactions. Part XV. For Part XIV, see ref. 1. +Dedicated to Professor Sumio Umezawa on the occasion of his 73rd birthday and the 25th anniversary of the Microbial Chemistry Research Foundation. **Concerned with the thermodynamic stabilities of some products, and already reported in preliminary formrl.

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