Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction
| dc.contributor.author | Straminelli, Leonardo | |
| dc.contributor.author | Vicentini, Francesco | |
| dc.contributor.author | Di Sabato, Antonio | |
| dc.contributor.author | Montone, Carmela Maria | |
| dc.contributor.author | Cavaliere, Chiara | |
| dc.contributor.author | Rissanen, Kari | |
| dc.contributor.author | Leonelli, Francesca | |
| dc.contributor.author | Vetica, Fabrizio | |
| dc.date.accessioned | 2022-08-22T09:59:57Z | |
| dc.date.available | 2022-08-22T09:59:57Z | |
| dc.date.issued | 2022 | |
| dc.identifier.citation | Straminelli, L., Vicentini, F., Di Sabato, A., Montone, C. M., Cavaliere, C., Rissanen, K., Leonelli, F., & Vetica, F. (2022). Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction. <i>Journal of Organic Chemistry</i>, <i>87</i>(15), 10454-10461. <a href="https://doi.org/10.1021/acs.joc.2c01046" target="_blank">https://doi.org/10.1021/acs.joc.2c01046</a> | |
| dc.identifier.other | CONVID_150935357 | |
| dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/82754 | |
| dc.description.abstract | 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). | en |
| dc.format.mimetype | application/pdf | |
| dc.language.iso | eng | |
| dc.publisher | American Chemical Society (ACS) | |
| dc.relation.ispartofseries | Journal of Organic Chemistry | |
| dc.rights | CC BY 4.0 | |
| dc.title | Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction | |
| dc.type | article | |
| dc.identifier.urn | URN:NBN:fi:jyu-202208224292 | |
| dc.contributor.laitos | Kemian laitos | fi |
| dc.contributor.laitos | Department of Chemistry | en |
| dc.contributor.oppiaine | Orgaaninen kemia | fi |
| dc.contributor.oppiaine | Organic Chemistry | en |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
| dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
| dc.description.reviewstatus | peerReviewed | |
| dc.format.pagerange | 10454-10461 | |
| dc.relation.issn | 0022-3263 | |
| dc.relation.numberinseries | 15 | |
| dc.relation.volume | 87 | |
| dc.type.version | publishedVersion | |
| dc.rights.copyright | © 2022 The Authors. Published by American Chemical Society | |
| dc.rights.accesslevel | openAccess | fi |
| dc.subject.yso | kemiallinen synteesi | |
| dc.subject.yso | orgaaninen kemia | |
| dc.format.content | fulltext | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p8468 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p11902 | |
| dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
| dc.relation.doi | 10.1021/acs.joc.2c01046 | |
| jyx.fundinginformation | The authors gratefully thank the colleagues at Sapienza University of Rome (Prof. Patrizia Gentili, Prof. Marta Feroci, Prof. Marco Bella), Dr. Giuliana Righi, and the Institute of Biological Systems (ISB) of the Italian National Research Council (CNR) for the donation of chemicals. Financial support from Sapienza University of Rome (Grant Number RP12117A5C0CA0CC) is gratefully acknowledged. | |
| dc.type.okm | A1 |
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