Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition

We report a desymmetrization of cyclohexadienones by intramolecular conjugate addition of a tethered dithiane nucleophile. Mild reaction conditions allow the formation of diversely functionalized fused bicyclic lactones. The products participate in facially selective additions from the convex surfac...

Descripción completa

Detalles Bibliográficos
Autores principales: Horwitz, Matthew A, Massolo, Elisabetta, Johnson, Jeffrey S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433211/
https://www.ncbi.nlm.nih.gov/pubmed/28546832
http://dx.doi.org/10.3762/bjoc.13.75
_version_ 1783236806524796928
author Horwitz, Matthew A
Massolo, Elisabetta
Johnson, Jeffrey S
author_facet Horwitz, Matthew A
Massolo, Elisabetta
Johnson, Jeffrey S
author_sort Horwitz, Matthew A
collection PubMed
description We report a desymmetrization of cyclohexadienones by intramolecular conjugate addition of a tethered dithiane nucleophile. Mild reaction conditions allow the formation of diversely functionalized fused bicyclic lactones. The products participate in facially selective additions from the convex surface, leading to allylic alcohol derivatives.
format Online
Article
Text
id pubmed-5433211
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-54332112017-05-25 Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition Horwitz, Matthew A Massolo, Elisabetta Johnson, Jeffrey S Beilstein J Org Chem Letter We report a desymmetrization of cyclohexadienones by intramolecular conjugate addition of a tethered dithiane nucleophile. Mild reaction conditions allow the formation of diversely functionalized fused bicyclic lactones. The products participate in facially selective additions from the convex surface, leading to allylic alcohol derivatives. Beilstein-Institut 2017-04-24 /pmc/articles/PMC5433211/ /pubmed/28546832 http://dx.doi.org/10.3762/bjoc.13.75 Text en Copyright © 2017, Horwitz et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Horwitz, Matthew A
Massolo, Elisabetta
Johnson, Jeffrey S
Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
title Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
title_full Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
title_fullStr Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
title_full_unstemmed Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
title_short Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
title_sort phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433211/
https://www.ncbi.nlm.nih.gov/pubmed/28546832
http://dx.doi.org/10.3762/bjoc.13.75
work_keys_str_mv AT horwitzmatthewa phosphazenecatalyzeddesymmetrizationofcyclohexadienonesbydithianeaddition
AT massoloelisabetta phosphazenecatalyzeddesymmetrizationofcyclohexadienonesbydithianeaddition
AT johnsonjeffreys phosphazenecatalyzeddesymmetrizationofcyclohexadienonesbydithianeaddition

Ejemplares similares