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Origin of π-Facial Stereoselectivity in Thiophene 1-Oxide Cycloadditions

We report a DFT computational study (M06–2X) of π-facial selectivity in the Diels—Alder reactions of thiophene 1-oxide. The preference for the syn cycloaddition arises because the ground state geometry of thiophene 1-oxide is predistorted into an envelope conformation that resembles the syn transiti...

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Detalhes bibliográficos
Publicado no:J Org Chem
Main Authors: Levandowski, Brian J., Herath, Dinushka, Gallup, Nathan M., Houk, K N
Formato: Artigo
Idioma:Inglês
Publicado em: 2018
Assuntos:
Acesso em linha:https://ncbi.nlm.nih.gov/pmc/articles/PMC6314815/
https://ncbi.nlm.nih.gov/pubmed/29360357
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/acs.joc.7b03016
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