Quaternary Stereogenic Centers Through Enantioselective Heck Arylation Of Acyclic Olefins With Aryldiazonium Salts: Application In A Concise Synthesis Of (r)-verapamil

dc.creatorOliveira
dc.creatorCaio C.; Pfaltz
dc.creatorAndreas; Duarte Correia
dc.creatorCarlos Roque
dc.date2015-Nov
dc.date2016-06-07T13:17:22Z
dc.date2016-06-07T13:17:22Z
dc.date.accessioned2018-03-29T01:37:56Z
dc.date.available2018-03-29T01:37:56Z
dc.identifier
dc.identifierQuaternary Stereogenic Centers Through Enantioselective Heck Arylation Of Acyclic Olefins With Aryldiazonium Salts: Application In A Concise Synthesis Of (r)-verapamil. Wiley-v C H Verlag Gmbh, v. 54, p. 14036-14039 Nov-2015.
dc.identifier1433-7851
dc.identifierWOS:000367722500033
dc.identifier10.1002/anie.201507927
dc.identifierhttp://onlinelibrary.wiley.com/doi/10.1002/anie.201507927/epdf
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/242307
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1306005
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionWe describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine-and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to > 99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil.
dc.description54
dc.description47
dc.description
dc.description14036
dc.description14039
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionSwiss National Science Foundation
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionFAPESP [2013/07600-3, 2014/00588-0]
dc.description
dc.description
dc.description
dc.languageen
dc.publisherWILEY-V C H VERLAG GMBH
dc.publisher
dc.publisherWEINHEIM
dc.relationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
dc.rightsfechado
dc.sourceWOS
dc.subjectRedox-relay Strategy
dc.subjectAlkenyl Alcohols
dc.subjectAsymmetric Heck
dc.subjectCoupling Reactions
dc.subjectOxazoline Ligands
dc.subjectCyclic Olefins
dc.subjectAryl Halides
dc.subjectCatalysis
dc.subjectDesymmetrization
dc.subjectHydrosilylation
dc.titleQuaternary Stereogenic Centers Through Enantioselective Heck Arylation Of Acyclic Olefins With Aryldiazonium Salts: Application In A Concise Synthesis Of (r)-verapamil
dc.typeArtículos de revistas


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