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Current Organic Synthesis

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ISSN (Online): 1875-6271

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Review Article

Chemistry of Unsymmetrical C1-Substituted Oxabenzonorbornadienes

Author(s): Austin Pounder, Angel Ho, Matthew Macleod and William Tam*

Volume 18, Issue 5, 2021

Published on: 05 January, 2021

Page: [446 - 474] Pages: 29

DOI: 10.2174/1570179417666210105121115

Price: $65

Abstract

Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate, which can be readily activated by transition metal complexes with great face selectivity due to its dual-faced nature and intrinsic angle strain on the alkene. To date, the understanding of transition-metal catalyzed reactions of OBD itself has burgeoned; however, this has not been the case for unsymmetrical OBDs. Throughout the development of these reactions, the nature of C1-substituent has proven to have a profound effect on both the reactivity and selectivity of the outcome of the reaction. Upon substitution, different modes of reactivity arise, contributing to the possibility of multiple stereo-, regio-, and in extreme cases, constitutional isomers, which can provide unique means of constructing a variety of synthetically useful cyclic frameworks. To maximize selectivity, an understanding of bridgehead substituent effects is crucial. To that end, this review outlines hitherto reported examples of bridgehead substituent effects on the chemistry of unsymmetrical C1-substituted OBDs.

Keywords: Oxabenzonorbornadiene, unsymmetrical oxabenzonorbornadiene, transition-metal-catalysis, ring-opening, cycloaddition, isomerization, substituent effects, regioselectivity.

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