Journal
ORGANIC LETTERS
Volume 20, Issue 24, Pages 7888-7892Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03440
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Funding
- Chinese NSF [21702217]
- 1000-Youth Talents Plan
- Shanghai-Youth Talent
- Shanghai-Technology Innovation Action Plan [18JC1415300]
- 100 Talent Program of the Chinese Academy of Sciences
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A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N-H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative coupling annulation of allylic sulfones without using peroxides or any metal oxidants. This developed protocol affords 7-membered ring heterocyclic compounds incorporating both sulfone-containing amino acid esters and one quaternary carbon center. Mechanistic studies indicate that an unusual umpolung of glycine occurred in this annulation.
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