Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction

[Image: see text] A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a high...

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Autores principales: Straminelli, Leonardo, Vicentini, Francesco, Di Sabato, Antonio, Montone, Carmela Maria, Cavaliere, Chiara, Rissanen, Kari, Leonelli, Francesca, Vetica, Fabrizio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9365295/
https://www.ncbi.nlm.nih.gov/pubmed/35875873
http://dx.doi.org/10.1021/acs.joc.2c01046
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author Straminelli, Leonardo
Vicentini, Francesco
Di Sabato, Antonio
Montone, Carmela Maria
Cavaliere, Chiara
Rissanen, Kari
Leonelli, Francesca
Vetica, Fabrizio
author_facet Straminelli, Leonardo
Vicentini, Francesco
Di Sabato, Antonio
Montone, Carmela Maria
Cavaliere, Chiara
Rissanen, Kari
Leonelli, Francesca
Vetica, Fabrizio
author_sort Straminelli, Leonardo
collection PubMed
description [Image: see text] A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a highly atom-economical Michael–domino Michael/aldol reaction sequence was optimized, yielding variously functionalized spiro-decalin oxindoles with excellent stereoselectivity (>99:1 dr, up to 92% ee).
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spelling pubmed-93652952022-08-11 Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction Straminelli, Leonardo Vicentini, Francesco Di Sabato, Antonio Montone, Carmela Maria Cavaliere, Chiara Rissanen, Kari Leonelli, Francesca Vetica, Fabrizio J Org Chem [Image: see text] A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a highly atom-economical Michael–domino Michael/aldol reaction sequence was optimized, yielding variously functionalized spiro-decalin oxindoles with excellent stereoselectivity (>99:1 dr, up to 92% ee). American Chemical Society 2022-07-25 2022-08-05 /pmc/articles/PMC9365295/ /pubmed/35875873 http://dx.doi.org/10.1021/acs.joc.2c01046 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Straminelli, Leonardo
Vicentini, Francesco
Di Sabato, Antonio
Montone, Carmela Maria
Cavaliere, Chiara
Rissanen, Kari
Leonelli, Francesca
Vetica, Fabrizio
Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction
title Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction
title_full Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction
title_fullStr Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction
title_full_unstemmed Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction
title_short Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction
title_sort stereoselective synthesis of spiro-decalin oxindole derivatives via sequential organocatalytic michael–domino michael/aldol reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9365295/
https://www.ncbi.nlm.nih.gov/pubmed/35875873
http://dx.doi.org/10.1021/acs.joc.2c01046
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