Synthesis of (+)-(Neomenthylsulfonyl)methyl Isocyanide. Synthesis and Absolute Configuration of (R)-(+)-2-Methylcyclobutanone and (S)-(-)-2-Methylcyclobutanone

Article abstract of DOI:10.1021/jo00338a019

Menthol is used for the synthesis of optically pure (+)-(neomenthylsulfonyl)methyl isocyanide (NeSMIC, 8), which is the first chiral sulfonylmethyl isocyanide reported.This NeSMIC is applied to a two-step synthesis of (R)-(+)-2-methylcyclobutanone (12), as well as its enantiomer (11), neither of which have been reported previously.The absolute configurations of 11 and 12 are determined by the octant rule and by an independent chiral synthesis.