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Dual Re V Catalysis in One‐Pot Consecutive Meyer–Schuster and Diels–Alder Reactions
Author(s) -
Bugoni Serena,
Porta Alessio,
Valiullina Zuleykha,
Zai Giuseppe,
Vidari Giovanni
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600926
Subject(s) - chemistry , cycloaddition , stereoselectivity , catalysis , selectivity , rhenium , diels–alder reaction , medicinal chemistry , computational chemistry , organic chemistry
A readily available oxo‐Re V catalyst has been shown to promote a one‐pot multistep process that involves the Meyer–Schuster rearrangement of alkynols followed by the Diels–Alder cycloaddition of the resulting enones. These reactions were performed under mild conditions in the presence of 5 mol‐% of the catalyst to afford the cycloadducts in good yields with almost 100 % endo stereoselectivity. In‐depth computational studies of the cycloaddition mechanism provided the preferred geometry of the rhenium complex in the transition state (TS) and corroborated the experimental endo selectivity.