Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage

An efficient and convenient synthesis of highly functionalized dihydropyrans has been achieved through rhodium(i)-catalysed tandem C(sp(3))–C(sp(3)) bond cleavage and annulation of oxetanols with alkynes. An enantioselective version was enabled using a Binaphine ligand. Excellent site-selectivity an...

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Detalles Bibliográficos
Autores principales: Guo, Rui, Zheng, Xinxin, Zhang, Dayong, Zhang, Guozhu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5380880/
https://www.ncbi.nlm.nih.gov/pubmed/28451367
http://dx.doi.org/10.1039/c6sc05246k
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author Guo, Rui
Zheng, Xinxin
Zhang, Dayong
Zhang, Guozhu
author_facet Guo, Rui
Zheng, Xinxin
Zhang, Dayong
Zhang, Guozhu
author_sort Guo, Rui
collection PubMed
description An efficient and convenient synthesis of highly functionalized dihydropyrans has been achieved through rhodium(i)-catalysed tandem C(sp(3))–C(sp(3)) bond cleavage and annulation of oxetanols with alkynes. An enantioselective version was enabled using a Binaphine ligand. Excellent site-selectivity and remarkable enantioretention are obtained for 2-substituted oxetanols.
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spelling pubmed-53808802017-04-27 Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage Guo, Rui Zheng, Xinxin Zhang, Dayong Zhang, Guozhu Chem Sci Chemistry An efficient and convenient synthesis of highly functionalized dihydropyrans has been achieved through rhodium(i)-catalysed tandem C(sp(3))–C(sp(3)) bond cleavage and annulation of oxetanols with alkynes. An enantioselective version was enabled using a Binaphine ligand. Excellent site-selectivity and remarkable enantioretention are obtained for 2-substituted oxetanols. Royal Society of Chemistry 2017-04-01 2017-01-23 /pmc/articles/PMC5380880/ /pubmed/28451367 http://dx.doi.org/10.1039/c6sc05246k Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Guo, Rui
Zheng, Xinxin
Zhang, Dayong
Zhang, Guozhu
Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage
title Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage
title_full Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage
title_fullStr Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage
title_full_unstemmed Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage
title_short Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp(3))–C(sp(3)) bond cleavage
title_sort rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through c(sp(3))–c(sp(3)) bond cleavage
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5380880/
https://www.ncbi.nlm.nih.gov/pubmed/28451367
http://dx.doi.org/10.1039/c6sc05246k
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AT zhangdayong rhodiumicatalyzedstereoselective42cycloadditionofoxetanolswithalkynesthroughcsp3csp3bondcleavage
AT zhangguozhu rhodiumicatalyzedstereoselective42cycloadditionofoxetanolswithalkynesthroughcsp3csp3bondcleavage

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