## 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 enga
Nucleophilic addition reactions of 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-d-erythro-hex-2-enitol and its 5a-carba derivative
โ Scribed by Akinori Seta; Shinji Ito; Kiyohisa Tokuda; Takeshi Tamura; Yaeko Konda; Tohru Sakakibara
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 648 KB
- Volume
- 267
- Category
- Article
- ISSN
- 0008-6215
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โฆ Synopsis
Reactions of the title compounds with several nucelophiles suggested that the ring oxygen atom (0-5) accelerated the reactivity of the nitro alkene moiety, but scarcely affected the stereoselectivity of the nucleophilic attack.
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## Electrophile (bromine, iodine, mercuric acetate, mercuric trifluoroacetate, phenylselenyl chloride)-mediated cyclization of 6-0-benzyl-1,2-dideoxy-3,4-0isopropylidene-D-ribo-hex-l-enitol (2) led exclusively to l-substituted derivatives of 2,5-anhydro-6-0-benzyl-3,4-O-isopropylidene-D-altro-hex
The 1,6-anhydro-2,3-dideoxy-B-D-erythro-/-threo-hex-2-enopyranoses 7-12 are valuable synthons for the preparation of structurally diverse natural productP, because (a) the rigid [3.2. llbicyclic framework facilitates highly stereo-and regio-selective reactionP, (b) each contains a reactive double bo