4.7 Article

Zinc-Mediated Diastereoselective Synthesis of 3-Amino Oxindoles by Addition of Methyl and Terminal Alkynes to N-tert-Butanesulfinyl Ketimines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 7, Pages 3311-3317

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo300110a

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Funding

  1. National Natural Science Foundation of China [20932003, 90813012]
  2. Ministry of Science and Technology of China [2012ZX09504-001-003]
  3. Fundamental Research Funds for the Central Universities [lzujbky-2010-126]

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A zinc-mediated addition of methyl and terminal alkyines to chiral N-tert-butanesulfinyl ketimines for the preparation of optical quaternary 3-amino oxindoles was reported. In general, the operationally simple reaction affords the desired products in high yields and good to excellent diastereoselectivities. Subsequent convenient cleavage of sulfinyl protecting group under mild conditions was presented without racemization.

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