Silver‐Catalyzed One‐Pot Access to Diastereoselective Benzooxepinopyrroles via Formal (5+2)‐Annulation of Donor‐/Acceptor‐Type Aryl Vinyl Diazosuccinimide with Ketones

A silver triflimide catalyzed one‐pot protocol for the diastereoselective synthesis of dihydrobenzoxepines has been developed. Silver triflimide was found to be an efficient catalyst for the formal (5+2)‐cycloaddition to access dihydrobenzoxepines as a single diastereomer using vinyl diazosuccinimid...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2022-04, Vol.11 (4)
Main Authors: Laha, Debasish, Meher, Kajal B, Bankar, Onkar S, Bhat, Ramakrishna G
Format: Article
Language:English
Subjects:
Catalysis
Chemical reactions
Cycloaddition
Ketones
NMR
Nuclear magnetic resonance
Organic chemistry
Pyrroles
Stereoselectivity
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Summary:A silver triflimide catalyzed one‐pot protocol for the diastereoselective synthesis of dihydrobenzoxepines has been developed. Silver triflimide was found to be an efficient catalyst for the formal (5+2)‐cycloaddition to access dihydrobenzoxepines as a single diastereomer using vinyl diazosuccinimides as 5‐C‐synthons and ketones. An unmet challenge of utilizing the donor‐/acceptor‐type vinyl diazosuccinimides as 5‐C‐synthons under silver‐catalysis is presented. This protocol was found to be highly regio‐, chemo‐ and diastereoselective, and works well with aliphatic as well as aromatic methyl ketones bearing electron deactivating as well as donating groups to afford dihydrobenzo[5,6]oxepino[2,3‐c]pyrroles. The control experiments and time‐dependent NMR studies revealed the plausible mechanism of this transformation. The protocol also proved to be scalable on the gram‐scale synthesis.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200062