Journal
ORGANIC LETTERS
Volume 21, Issue 20, Pages 8383-8388Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03159
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Funding
- National Natural Science Foundation of China [21871292]
- Yunnan University
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Treating chiral N-tert-butanesulfinyl ketimines with potassium hexamethyldisilazide (or potassium tert-butoxide) and methyl triflate gives N-methylated N-tert-butanesulfinyl enamine intermediates that undergo stereoselective [2,3]-rearrangement to afford alpha-sulfenyloxy ketones with excellent enantiopurities. This cascade of enamination-N-methylation rearrangement was even used to generate acyclic tertiary alpha-hydroxy ketones bearing two alpha-substituents showing negligible differences in bulkiness, such as methyl and ethyl groups.
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