221638-07-9

Upstream product

• 196409-39-9 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-N-methoxy-N-methyl-3-((R)-toluene-4-sulfinyl)-propionamide 
• 196409-37-7 (R)-N-methoxy-N-methyl-2-oxo-3-(p-tolylsulfinyl)propanamide 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 196409-48-0 (S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-((R)-toluene-4-sulfinyl)-butan-2-one 

Relevant academic research and scientific papers

Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols. Correction of the relative configuration by X-ray and chemical correlation to goniobutenolides A and B

In our recent report on the enantioselective synthesis of syn and anti 1,2-diols from oxalyl-di-(N-methyl-N-methoxyamide), an unfortunate sample inversion for 13C NMR analysis led us to an incorrect attribution of their relative configurations. We report now the correction of the configurations of these diols by X-ray analysis and chemical correlation to two known natural products, goniobutenolides A and B.

Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols

A new route to enantiopure syn and anti 1,2-diols is described from oxalyl-di-(N-methyl-N-methoxyamide) via the corresponding β-ketosulfoxide. This is the first report of the stereoselective reduction of a γ-keto-β-hydroxysulfoxide.