Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation

Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol-directed C(sp(2))-H functionalization and oxidative annulation with alkynes to give spiroindenes containing all-carbon quaternary stereocenters. High selectivity between two possible directing groups, as well as control o...

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Autores principales: Reddy Chidipudi, Suresh, Burns, David J, Khan, Imtiaz, Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648053/
https://www.ncbi.nlm.nih.gov/pubmed/26404643
http://dx.doi.org/10.1002/anie.201507029
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author Reddy Chidipudi, Suresh
Burns, David J
Khan, Imtiaz
Lam, Hon Wai
author_facet Reddy Chidipudi, Suresh
Burns, David J
Khan, Imtiaz
Lam, Hon Wai
author_sort Reddy Chidipudi, Suresh
collection PubMed
description Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol-directed C(sp(2))-H functionalization and oxidative annulation with alkynes to give spiroindenes containing all-carbon quaternary stereocenters. High selectivity between two possible directing groups, as well as control of the direction of rotation in the isomerization of an O-bound rhodium enolate into the C-bound isomer, appear to be critical for high enantiomeric excesses.
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spelling pubmed-46480532015-11-24 Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation Reddy Chidipudi, Suresh Burns, David J Khan, Imtiaz Lam, Hon Wai Angew Chem Int Ed Engl Communications Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol-directed C(sp(2))-H functionalization and oxidative annulation with alkynes to give spiroindenes containing all-carbon quaternary stereocenters. High selectivity between two possible directing groups, as well as control of the direction of rotation in the isomerization of an O-bound rhodium enolate into the C-bound isomer, appear to be critical for high enantiomeric excesses. WILEY-VCH Verlag 2015-11-16 2015-09-25 /pmc/articles/PMC4648053/ /pubmed/26404643 http://dx.doi.org/10.1002/anie.201507029 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Reddy Chidipudi, Suresh
Burns, David J
Khan, Imtiaz
Lam, Hon Wai
Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
title Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
title_full Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
title_fullStr Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
title_full_unstemmed Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
title_short Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
title_sort enantioselective synthesis of spiroindenes by enol-directed rhodium(iii)-catalyzed c–h functionalization and spiroannulation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648053/
https://www.ncbi.nlm.nih.gov/pubmed/26404643
http://dx.doi.org/10.1002/anie.201507029
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