Stereoselective Insertion of Benzynes into Lawsones: Synthesis of Biologically Important Benzannulated Bicyclo[3.3.0]octanes

A Suresh Kumar; Guguloth Thirupathi; G Surendra Reddy; Dhevalapally B Ramachary

doi:10.1002/chem.201805798

Stereoselective Insertion of Benzynes into Lawsones: Synthesis of Biologically Important Benzannulated Bicyclo[3.3.0]octanes

Chemistry. 2019 Jan 24;25(5):1177-1183. doi: 10.1002/chem.201805798. Epub 2019 Jan 4.

Authors

A Suresh Kumar¹, Guguloth Thirupathi¹, G Surendra Reddy¹, Dhevalapally B Ramachary¹

Affiliation

¹ Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-, 500 046, India.

PMID: 30515913
DOI: 10.1002/chem.201805798

Abstract

An ideal stereoselective insertion of in situ generated benzynes into lawsones through domino formal [2+2]-cycloaddition followed by rearrangement is disclosed. The reaction allowed for the preparation of biologically important benzannulated bicyclo[3.3.0]octanes in good yields and with excellent selectivities by using simple substrates and conditions.

Keywords: [3+2]-cycloaddition; arynes; bicyclo[3.3.0]octanes; catalysis; lawsones.

Grants and funding

Grant No.: EMR/2015/000860/Science and Engineering Research Board