Journal
ORGANIC LETTERS
Volume 24, Issue 42, Pages 7817-7821Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03171
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Funding
- National Natural Science Foundation of China [21871292, 22161048]
- Yunnan University
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In this study, a method for the hydroxymethylation of alpha-branched ketimines using formaldehyde equivalents was developed, allowing for the stereoselective construction of acyclic quaternary stereocenters bearing two similar substituents.
Hydroxymethylation of alpha-branched N-tert-butanesul-finyl ketimines with formaldehyde equivalents was developed to stereoselectively construct acyclic quaternary stereocenters bearing two sterically and electronically similar substituents. The stereo-selective tBuOK-promoted alpha-deprotonation of acyclic ketimines allowed for the stereodefined formation of fully substituted aza-enolates, followed by facially selective C-C bond formation involving formaldehyde formed in situ, yielding alpha-hydroxymethylated products with precise stereocontrol.
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