4.8 Article

Asymmetric Construction of Spiro[thiopyranoindole-benzoisothiazole] Scaffold via a Formal [3+3] Spiroannulation

Journal

ORGANIC LETTERS
Volume 17, Issue 17, Pages 4188-4191

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01951

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Funding

  1. National Natural Science Foundation of China [21272166]
  2. Natural Science Foundation of the Jiangsu Higher Education Institutions [13KJA150004]
  3. Program for New Century Excellent Talents in University [NCET-12-0743]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
  5. Scientific and Technologic Infrastructure of Suzhou [SZS201207]

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An enantioselective formal thio [3 + 3] spiroannulation reaction of indoline-2-thiones to 1-azadienes has been developed by the use of a quinine-derived bifunctional tertiary amine-thiourea catalyst, which furnished a series of optically active spiro [thiopyranoindole-benzoisothiazole] heterocycles with a Spiro quaternary C-N/C-S stereogenic centers in high yields with good to excellent diastereo- and enantioselectivities.

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