A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H

[Image: see text] A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected form...

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Autores principales: Shockley, Samantha E., Holder, Jeffrey C., Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4275150/
https://www.ncbi.nlm.nih.gov/pubmed/25489925
http://dx.doi.org/10.1021/ol5031537
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author Shockley, Samantha E.
Holder, Jeffrey C.
Stoltz, Brian M.
author_facet Shockley, Samantha E.
Holder, Jeffrey C.
Stoltz, Brian M.
author_sort Shockley, Samantha E.
collection PubMed
description [Image: see text] A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett constants for para-substituted arenes enabled the rational design of a highly enantioselective conjugate addition substrate that led to the completion of the formal synthesis.
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spelling pubmed-42751502015-12-09 A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H Shockley, Samantha E. Holder, Jeffrey C. Stoltz, Brian M. Org Lett [Image: see text] A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett constants for para-substituted arenes enabled the rational design of a highly enantioselective conjugate addition substrate that led to the completion of the formal synthesis. American Chemical Society 2014-12-09 2014-12-19 /pmc/articles/PMC4275150/ /pubmed/25489925 http://dx.doi.org/10.1021/ol5031537 Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Shockley, Samantha E.
Holder, Jeffrey C.
Stoltz, Brian M.
A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
title A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
title_full A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
title_fullStr A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
title_full_unstemmed A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
title_short A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
title_sort catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone h
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4275150/
https://www.ncbi.nlm.nih.gov/pubmed/25489925
http://dx.doi.org/10.1021/ol5031537
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