Chemoenzymatic and Enantiomeric Switching Regimes Enabling the Synthesis of Homochiral Cyclohexa-2,5-dienones Incorporating All-Carbon Quaternary Centers

Autor:	Sebastian Ye, Martin G. Banwell
Rok vydání:	2021
Předmět:	Chemistry Metabolite Organic Chemistry chemistry.chemical_element Stereoisomerism Sequence (biology) Combinatorial chemistry Carbon Lithium hydroxide chemistry.chemical_compound Fragmentation (mass spectrometry) Reaction sequence Enantiomer Enone
Zdroj:	The Journal of Organic Chemistry. 86:15403-15412
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c01931
Popis:	The enantiomerically pure, bromobenzene-derived metabolite 5 has been transformed into enone 20 using a reaction sequence involving Suzuki-Miyaura cross-coupling and Eschenmoser-Claisen rearrangement processes. Treatment of compound 20 with lithium hydroxide results in an acetonide fragmentation reaction that delivers the 4,4-disubstituted cyclohexa-2,5-dienone 21, reductive de-oxygenation of which leads to congener 22. A closely related sequence of reactions can be used to convert the same homochiral starting material 5 into compound ent-22.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::47e9b9b3c4c50ef6e79e310690a60d68 https://doi.org/10.1021/acs.joc.1c01931 Zobrazit plný text záznamu