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A facile preparation of α-hydrazino-α,β-unsaturated ketones via aza-Baylis-Hillman reaction
✍ Scribed by Akio Kamimura; Yoko Gunjigake; Hiromasa Mitsudera; Shuji Yokoyama
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 126 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
ct-(N,N'-Bisalkoxycarbonyl)hydrazino-et,~-unsaturated ketones are readily prepared via the aza-Baylis-Hillman reaction of alkyl vinyl ketones and azodicarboxylate esters.
📜 SIMILAR VOLUMES
AbstractÐThe Baylis±Hillman reaction can be drastically affected by the reaction temperature and Lewis base. When the reaction was carried out at ,2208C using methyl sul®de as a Lewis base in the presence of titanium(IV) chloride, the chlorinated compound 1 was obtained as the major product. However
a,@-Epoxy ketones 2\_, upon treatment with two equivalents of trialkylstannylmethyllithium 1, afforded cyclopropanols 2 as a single product in acyclic system, and a mixture of cyclopropanols 2 and methylene 1,2-diols 2 in cyclic system. Under acidic conditions, the cyclopropanols gave p,y-unsaturate