85260-53-3Relevant academic research and scientific papers
Dess-Martin periodinane oxidative rearrangement for preparation of α-keto thioesters
Sanichar, Randy,Carroll, Ciaran,Kimmis, Ryan,Reiz, Bela,Vederas, John C.
supporting information, p. 593 - 597 (2018/02/09)
A Dess-Martin Periodinane (DMP) mediated oxidative rearrangement reaction was uncovered. The reaction proceeds via oxidation of a β-hydroxy thioester to a β-keto thioester, followed by an α-hydroxylation and then further oxidation to form a vicinal thioester tricarbonyl. This product then rearranges, extruding CO2, to form an α-keto product. The mechanism of the rearrangement was elucidated using 13C labelling and analysis of the intermediates as well as the products of the reaction. This efficient process allows for easy preparation of α-keto thioesters which are potential intermediates in the synthesis of pharmaceutically important heterocyclic scaffolds such as quinoxalinones.
SYNTHETIC CONTROL LEADING TO CHIRAL COMPOUNDS
Mukaiyama, Teruaki,Iwasawa, Nobuharu,Stevens, Rodney W.,Haga, Toru
, p. 1381 - 1390 (2007/10/02)
A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds.The reaction is extended to a highly enantioselective cross aldol reaction employing chiral dia
HIGHLY ENANTIOSELECTIVE ALDOL-TYPE REACTION OF 3-ACETYLTHIAZOLIDINE-2-THIONE WITH ACHIRAL ALDEHYDES
Iwasawa, Nobuharu,Mukaiyama, Teruaki
, p. 297 - 298 (2007/10/02)
A highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehydes is achieved via divalent tin enolate employing chiral diamine derived from (S)-proline as a ligand.
STANNOUS TRIFLATE MEDIATED ALDOL REACTION OF 3-ACYLTHIAZOLIDINE-2-THIONE: A CONVENIENT METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF β-HYDROXY ALDEHYDE AND β-HYDROXY CARBOXYLIC ACID DERIVATIVES
Mukaiyama, Teruaki,Iwasawa, Nobuharu
, p. 1903 - 1906 (2007/10/02)
Divalent tin enolates, formed from stannous triflate and 3-acylthiazolidine-2-thiones, react with aldehydes with erythro-selectivities.The adducts are easily transformed into β-hydroxy aldehyde and β-hydroxy carboxylic acid derivatives.
