139750-83-7Relevant academic research and scientific papers
Diastereoselective oxidation of menthyl arenesulfenates to sulfinates and access to enantioenriched aryl methyl sulfoxides
Hamel, Matthieu,Vazeux, Michel,Gulea, Mihaela
, p. 6137 - 6143 (2021/07/12)
Three aryl methyl sulfoxides were prepared via the following sequence: synthesis of the menthyl arenesulfenate from the corresponding thiol, diastereoselective oxidation leading to the sulfinate, then reaction with a Grignard reagent. The aryl moiety was substituted with a methyl ester on the ortho position or a nitro group on the ortho or the para position. The sulfenate esters were obtained in fair to excellent yield (42–82%). Four different oxidizing agents were tested to obtain the corresponding sulfinate esters with diastereomeric excesses (de) ranging from 10 to 48%. After separation of the diastereomers and reaction with methyl Grignard reagent, two enantiopure sulfoxides and one enantioenriched sulfoxide (32% ee) were obtained.
A convenient and highly diastereoselective synthesis of optically active sulfinate esters from sulfonyl chlorides under solid state conditions
Hajipour, Abdolreza,Islami, Fereshteh
, p. 461 - 462 (2007/10/03)
A manipulatively simple and rapid method for synthesis of chiral sulfinate esters 1 and 2 from sulfonyl chloride and trimethyl phosphite in solid phase conditions supported on silica gel is described. The chemical yields are good to excellent and diastereoselectivity is high.
Chiral Acetylenic Sulfoxide in Enantioselective Synthesis of Tetrahydroisoquinoline and Tetrahydro-β-carboline Alkaloids. Total Synthesis of (R)-(+)-Carnegine and (R)-(+)-Tetrahydroharman
Lee, Albert W. M.,Chan, Wing Hong,Tao, Yi,Lee, Yu Kai
, p. 477 - 482 (2007/10/02)
Michael addition of 2-(3,4-dimethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity.Optically pure (R)-(+)-carnegine and (R)-(+)-tetrahydroharman have been synthesized.
Chiral acetylenic sulfoxide in alkaloid synthesis. Total synthesis of (R)-(+)-carnegine
Lee,Chan,Lee
, p. 6861 - 6864 (2007/10/02)
Remarkable diastereoselectivity was observed in the cyclization of β-aminovinyl sulfoxide 5a prepared from chiral acetylenic sulfoxide 1a in acidic medium. The cyclized product 6a was then converted to (R)-(+)-carnegine.
