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dc.contributor.authorLiu, Richard
dc.contributor.authorZhou, Yujing
dc.contributor.authorYang, Yang
dc.contributor.authorBuchwald, Stephen Leffler
dc.date.accessioned2020-03-25T18:20:47Z
dc.date.available2020-03-25T18:20:47Z
dc.date.issued2019-01-27
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.urihttps://hdl.handle.net/1721.1/124335
dc.description.abstractAllene (C₃H₄) gas is produced and separated on million-metric-ton scale per year during petroleum refining but is rarely employed in organic synthesis. Meanwhile, the addition of an allyl group (C₃H₅) to ketones is among the most common and prototypical reactions in synthetic chemistry. Herein, we report that the combination of allene gas with inexpensive and environmentally benign hydrosilanes, such as PMHS, can serve as a replacement for stoichiometric quantities of allylmetal reagents, which are required in most enantioselective ketone allylation reactions. This process is catalyzed by copper catalyst and commercially available ligands, operates without specialized equipment or pressurization, and tolerates a broad range of functional groups. Furthermore, the exceptional chemoselectivity of this catalyst system enables industrially relevant C3 hydrocarbon mixtures of allene with methylacetylene and propylene to be applied directly. Based on our strategy, we anticipate the rapid development of methods that leverage this unexploited feedstock as an allyl anion surrogate.en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (grant GM58160)en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (grant GM58160–17S1)en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (grant GM122483)en_US
dc.language.isoen
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionof10.1021/jacs.8b13907en_US
dc.rightsArticle is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.en_US
dc.sourcePMCen_US
dc.subjectColloid and Surface Chemistryen_US
dc.subjectBiochemistryen_US
dc.subjectGeneral Chemistryen_US
dc.subjectCatalysisen_US
dc.titleEnantioselective Allylation Using Allene, a Petroleum Cracking Byproducten_US
dc.typeArticleen_US
dc.identifier.citationLiu, Richard Y., Yujing Zhou, Yang Yang and Stephen L. Buchwald. "Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct." ACS publications 141 (2019):2251-2256 © 2019 The Author(s)en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.relation.journalACS publicationsen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dc.date.updated2020-02-19T19:16:34Z
dspace.date.submission2020-02-19T19:16:36Z
mit.journal.volume141en_US
mit.journal.issue6en_US
mit.licensePUBLISHER_POLICY


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