Journal
CHEMICAL COMMUNICATIONS
Volume 58, Issue 70, Pages 9762-9765Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc03802a
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- CSIR, New Delhi
- SERB, New Delhi
- IIT Bombay
- UGC, New Delhi
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The TMSOTf-mediated reaction of alkynyl vinylogous carbonates unexpectedly generates 1,4-oxazepine and dihydropyran dienes through the transposition of an ethyl acrylate moiety via an intramolecular cascade Prins-type cyclization/retro-oxa-Michael reaction/cycloisomerisation. This atom-economical protocol selectively produces a specific E double bond geometry, and the dihydropyran dienes can be further transformed into polycyclic heterocycles using the Heck reaction.
TMSOTf-mediated reaction of alkynyl vinylogous carbonates serendipitously gave 1,4-oxazepine and dihydropyran dienes via transposition of an ethyl acrylate moiety involving intramolecular cascade Prins-type cyclization/retro-oxa-Michael reaction/cycloisomerisation. The developed atom-economical protocol selectively provides an E double bond geometry. Dihydropyran dienes could be reduced diastereoselectively using Et3SiH/TMSOTf or could be transformed into polycyclic heterocycles by Heck reaction.
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