Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine

We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57−76% yields and with 4−8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cyclohepteno...

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Veröffentlicht in:	Journal of organic chemistry 2003-04, Vol.68 (8), p.3049-3054
Hauptverfasser:	Posner, Gary H, Maxwell, John P, Kahraman, Mehmet
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Catalysis Chemistry Chemistry, Organic - methods Epoxy Compounds - chemistry Exact sciences and technology Indicators and Reagents Ketones - chemistry Kinetics Lignans - analysis Lignans - chemical synthesis Molecular Structure Nuclear Magnetic Resonance, Biomolecular Organic chemistry Preparations and properties Stereoisomerism
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