116487-06-0Relevant academic research and scientific papers
Asymmetric methylene transfer reactions I: Asymmetric synthesis of oxiranes from carbonyl compounds by methylene transfer reaction using chiral S-methyl-S-neomenthyl-N-tosyl sulfoximines
Taj,Soman
, p. 1513 - 1518 (1994)
The use of ylides prepared from (-)-S-methyl-S-neomenthyl-N-tosyl sulfoximine, 10a, and its epimer at sulfur, 10b, as methylene transfer reagents for the conversion of prochiral carbonyl compounds to oxiranes has yielded chiral oxiranes with 56-86% enantiomeric excess.
Synthesis of (+)-Neomenthanethiol and Some of Its Derivatives. A New Example of Asymmetric Induction in the Sulfoxide Synthesis
Mikolajczyk, Marian,Perlikowska, Wieslawa,Omelanczuk, Jan
, p. 1009 - 1012 (2007/10/02)
(+)-Neomenthanethiol (1b) with D20+53.9 deg (c=1.85, CHCl3), is prepared from (-)-menthol (2a) in three steps in 42percent overall yield. 1H- and 31P-NMR studies showed that the diastereomeric and optical purity of the product obtained is at least 95percent.Methylation of (+)-1b leads to (+)-methyl neomenthyl sulfide (11) which undergoes oxidation to the corresponding sulfoxide (+)-13 (a mixture of diastereomers in a 69:31 ratio) and sulfone (+)-12.
