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

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 se...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-01, Vol.25 (5), p.1177-1183
Main Authors: Kumar, A. Suresh, Thirupathi, Guguloth, Reddy, G. Surendra, Ramachary, Dhevalapally B.
Format: Article
Language:English
Subjects:
[3+2]-cycloaddition
arynes
bicyclo[3.3.0]octanes
catalysis
Chemistry
Cycloaddition
Insertion
lawsones
Octanes
Stereoselectivity
Substrates
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Summary: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. An ideal stereoselective insertion of in situ generated benzynes into lawsones through domino formal [2+2]‐cycloaddition–rearrangement is disclosed. The method gave access to biologically important benzannulated bicyclo[3.3.0]octanes in good yields and with excellent selectivities.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805798