Title:
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a,b-Unsaturated Gold(I) Carbenes by Tandem Cyclization and 1,5- Alkoxy Migration of 1,6-Enynes: Mechanisms and Applications
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Author:
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Calleja, Pilar; Pablo, Óscar; Ranieri, Beatrice; Gaydou, Morgane; Pitaval, Anthony; Moreno, María; Raducan, Mihai; Echavarren, Antonio M.
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Abstract:
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1,6-Enynes bearing OR groups at the propargyl position generate a,b-unsaturated gold(I)-carbenes/ gold(I) stabilized allyl cations that can be trapped by alkenes to form cyclopropanes or 1,3-diketones to give products of a- alkylation. The best migrating group is p-nitrophenyl ether, which leads to the corresponding products without racemi- zation. Thus, an improved formal synthesis of (+)-schisanwil- sonene A has been accomplished. The different competitive reaction pathways have been delineated computationally. |
Publication date:
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2016-08-16 |
Subject(s):
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53 |
Rights:
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L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/ |
Pages:
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13613 p. |
Document type:
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Article Article - Accepted version |
DOI:
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10.1002/chem.201602347
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