Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 1, Pages 30-34Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01625g
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Funding
- Natural Science Foundation of Shandong Province
- Special Funds of the Taishan Scholar Program of Shandong Province
- Shenzhen Innovation of Science and Technology Commission
- Guangdong Provincial Key Laboratory of Catalysis
- [ZR2021MB026]
- [tsqn201812047]
- [20200925151614002]
- [2020B121201002]
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This study achieved the enantioselective construction of chiral spiro N,N-acetal carbon stereocenters and axially chiral 3-arylindoles through a chiral phosphoric acid catalyzed annulation reaction. The reaction between alpha-(3-isoindolinonyl) propargylic alcohols and 1-(3-indolyl)naphthalen-2-ols resulted in a wide range of pyrrolo[1,2-a]indoles with enantioenriched spiro isoindolinone-indoline and atropisomeric naphthalenol frameworks. A possible mechanism was proposed based on control experiments and previous work.
Organocatalytic enantioselective construction of chiral spiro N,N-acetal carbon stereocenters and axially chiral 3-arylindoles has been achieved via a chiral phosphoric acid (CPA)-catalyzed (3 + 2) annulation of alpha-(3-isoindolinonyl) propargylic alcohols with 1-(3-indolyl)naphthalen-2-ols, affording a broad scope of pyrrolo[1,2-a]indoles bearing both enantioenriched spiro isoindolinone-indoline and atropisomeric naphthalenol frameworks. Based on control experiments and our previous work, a possible mechanism was proposed accordingly.
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