Journal
ORGANIC LETTERS
Volume 18, Issue 3, Pages 620-623Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00006
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Funding
- National Natural Science Foundation of China [21572262, U1403301, 21372255]
- YCSTTC Project of Xinjiang Uygur Autonomous Region [2013711017]
- Recruitment Program of Global Experts (Xinjiang Program)
- XTIPC [2015RC014]
- Graduate Innovation Projects of Changji University [2015YJSYB05]
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A silyllithium-initiated coupling of alpha-ketoamides with tert-butanesulfinylimines was developed for the efficient, stereoselective synthesis of enantioenriched alpha-(silyloxy)-beta-amino amides. Nucleophilic addition of silyllithium to alpha-ketoamides, followed by 1,2-Brook rearrangement, generates nucleophilic enolates, which are then intercepted by chiral imines to provide three-component coupling products. Use of alpha-ketoamides yields and diastereoselectivities in the resulting alpha-hydroxy-beta-amino acid derivatives.
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