73818-39-0Relevant articles and documents
Enantioselective Synthesis of 3,4-Dihydropyran-2-ones via Phase-Transfer-Catalyzed Addition-Cyclization of Acetylacetone to Cinnamic Thioesters
Destro, Dario,Bottinelli, Carlo,Ferrari, Ludovica,Albanese, Domenico C. M.,Bencivenni, Grazia,Gillick-Healy, Malachi W.,Kelly, Brian G.,Adamo, Mauro F. A.
supporting information, p. 5183 - 5192 (2020/04/10)
Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis of Cinchona-derived quaternary ammonium phenoxide that, in combination with inorganic bases, provided 3,4-dihydropyran-2-ones in yields of up to 93% and enantioselectivities of up to 88% enantiomeric excess.
Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols
Panchal, Heena,Clarke, Christopher,Bell, Charles,Karad, Somnath Narayan,Lewis, William,Lam, Hon Wai
supporting information, p. 12389 - 12392 (2018/11/20)
Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to give a broad range of substituted 3-methyleneindan-1-ols. Preliminary results of an enantioselective variant are also described.
Synthesis of (2RS,E)-3-Ethylidene-azetidine-2-carboxylic acid (rac. polyoximic acid)
Emmer, Gerhard
, p. 7165 - 7172 (2007/10/02)
Treatment of α-diazo β-ketoester 4 with a catalytic amount of rhodium (II) acetate followed by Wittig reaction with phosphorane 5 gave the isomeric phenylthioester derivative 6a and 6b. Reduction of 6a led to the corresponding allylic alcohol 7, which was further converted into the bromide 8. Dehalogenation of 8 with NaBH4/ DMF resulted in compound 9, which was deprotected with trifluoroacetic acid, giving racemic polyoximic acid (1).