Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene

Autor:	Kim Spielmann, Jean-Marc Campagne, Renata Marcia de Figueiredo
Přispěvatelé:	Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)
Rok vydání:	2017
Předmět:	Benzylic alcohol Stereospecificity [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Stereochemistry Hydrogenolysis Chemistry Organic Chemistry Stereoselectivity 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis
Zdroj:	Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2017, 82, pp.4737-4743. ⟨10.1021/acs.joc.7b00419⟩
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.7b00419
Popis:	International audience; A straightforward strategy for the syntheses of curcumene and ar-himachalene is reported. Synthetic highlights include a catalytic and asymmetric vinylogous Mukaiyama reaction and a stereospecific hydrogenolysis of a tertiary benzylic center using Pd/C or Ni/Raney catalysts. Notably, using Ni/Raney, the stereoselectivity outcome (inversion vs retention) of the hydrogenolysis depends on the tertiary benzylic alcohol substitution.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::bf471034fb3a9c402bbdc312ea622f5c https://doi.org/10.1021/acs.joc.7b00419 Zobrazit plný text záznamu