Controlling Stereoselectivity in Tribromide Mediated Oxidative Dearomatisations – Synthesis of Selective Spirofurano‐naphthalones

A series of ammonium tribromides were screened for exploring the role of ammonium counterpart attached to tribromides on generation of stereoselective spiro‐furans via oxidative dearomatisation of naphthols. The proposition enlightens a suitable combination of the ammonium tribromide and solvent emp...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-09, Vol.2019 (34), p.5894-5904
Main Authors: Sarkar, Debayan, Kuila, Puspendu, Sood, Devashish
Format: Article
Language:English
Subjects:
Dearomatisation
Diastereoselective
Furans
Gram‐scale
QATBs
Spiro‐furano naphthalone
Stereoselectivity
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Summary:A series of ammonium tribromides were screened for exploring the role of ammonium counterpart attached to tribromides on generation of stereoselective spiro‐furans via oxidative dearomatisation of naphthols. The proposition enlightens a suitable combination of the ammonium tribromide and solvent employed, deliver the best achieved diastereoselectivities. This in turn, has also envisioned the mechanistic aspects related to this category of reactions. The mentioned dearomative spiro‐furano naphthalones has also been successfully achieved on a large‐scale. A mild and highly stereocontrolled tribromide mediated synthesis of spiro‐furano naphthalones via a oxidative dearomatisation process is reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900974