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Synthesis 1987; 1987(11): 1009-1012
DOI: 10.1055/s-1987-28150
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Synthesis of (+)-Neomenthanethiol and Some of Its Derivatives. A New Example of Asymmetric Induction in the Sulfoxide Synthesis

Marian Mikołajczyk* , Wiesława Perlikowska, Jan Omelańczuk
  • *Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Organic Sulfur Compounds, Boczna 5 PL-90-362 Łódź, Poland
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Publication Date:
12 September 2002 (online)

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(+)-Neomenthanethiol (1b) with (c = 1.85, CHCl3), is prepared from (-)-menthol (2a) in three steps in 42% overall yield. 1H- and 31P-NMR studies showed that the diastereomeric and optical purity of the product obtained is at least 95%. 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.