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A new method for construction of cyclic enones via phosphonate anions

✍ Scribed by Toshiaki Furuta; Eriko Oshima; Yoshinori Yamamoto

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
787 KB
Volume
3
Category
Article
ISSN
1042-7163

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✦ Synopsis

The reaction of 2,2-disiibstituted 1,3-cyclohexanediones (1) with dimethyl methylphosphonate anion in the presence of trimethylsilyl chloride produces 3-substituted 2-tyclohexenones (2) in moderate to very good yields. This new overall reaction is accounted for by (1) attack of the phosphonate anion on a carbonyl group, (2) retro-aldol cleavage, (3) reorganization of the acidic proton, and (4) an intramolecular Wadsworth-Emmonds condensation. The new rearrangement is applied to a short synthesis of ( t )-a-acoradiene. The synthesis of 3-substituted 2-cyclopentenones (10) is accomplished via two-step processes.

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