129880-16-6Relevant articles and documents
Hydroxy-Directed Amidation of Carboxylic Acid Esters Using a Tantalum Alkoxide Catalyst
Tsuji, Hiroaki,Yamamoto, Hisashi
supporting information, p. 14218 - 14221 (2016/11/13)
We describe herein a new strategy for the chemoselective synthesis of amides by using a metal-catalyzed hydroxy-directed reaction. A hydroxy group located at the β-position of an ester group promoted the activation of a carbonyl group with a tantalum alkoxide catalyst followed by amidation reactions, leading to a wide variety of β-hydroxyamides with excellent chemeselectivity. The chemoselective amidation strategy can be extended to the catalytic synthesis of dipeptide derivatives, which remains challenging research subjects in modern organic synthesis.
Catalysis of Mukaiyama aldol reactions by a tricyclic aluminum alkoxide Lewis acid
Raders, Steven M.,Verkade, John G.
supporting information; experimental part, p. 5417 - 5428 (2009/12/08)
(Chemical Equation Presented) The Mukayiama aldol reaction of aldehydes is efficiently accomplished with a low concentration of the dimeric alumatrane catalyst 2 at mild or subambient temperatures. Our protocol tolerates a wide variety of electron-rich, neutral, and deficient aryl, alkyl, and heterocyclic aldehydes. A wide variety of enol silyl ethers are also tolerated. An intermediate that was isolated provides mechanistic information regarding the role of dimeric 2 in the Mukaiyama aldol reaction. Experimental evidence is presented for the stronger Lewis acidity of 5 compared with F3B.
Carbonylative ring opening of terminal epoxides at atmospheric pressure
Denmark, Scott E.,Ahmad, Moballigh
, p. 9630 - 9634 (2008/03/17)
(Chemical Equation Presented) The carbonylative opening of terminal epoxides under mild conditions has been developed using Co2-(CO) 8 as the catalyst. Under 1 atm of carbon monoxide and at room temperature in methanol, propylene oxide is converted to methyl 3-hydroxybutanoate in up to 89% yield. This transformation is general for many terminal epoxides bearing alkyl, alkenyl, aryl, alkoxy, chloromethyl, phthalimido, and acetal functional groups. The opening takes place without epimerization at the secondary stereocenter.