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dc.contributor.author
Srinivas Reddy, D.  
dc.contributor.author
Srinivas, Beduru  
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Rachineni, Kavitha  
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Jagadeesh, Bharatam  
dc.contributor.author
Sarotti, Ariel Marcelo  
dc.contributor.author
Mohapatra, Debendra K.  
dc.date.available
2021-12-22T16:56:39Z  
dc.date.issued
2021-05  
dc.identifier.citation
Srinivas Reddy, D.; Srinivas, Beduru; Rachineni, Kavitha; Jagadeesh, Bharatam; Sarotti, Ariel Marcelo; et al.; BF3·OEt2-Catalyzed Unexpected Stereoselective Formation of 2,4-trans-Diallyl-2-methyl-6-aryltetrahydro-2H-pyrans with Quaternary Stereocenters; American Chemical Society; Journal of Organic Chemistry; 86; 9; 5-2021; 6518-6527  
dc.identifier.issn
0022-3263  
dc.identifier.uri
http://hdl.handle.net/11336/149200  
dc.description.abstract
The present manuscript describes a convenient, mild, and highly stereoselective method for the allylation of δ-hydroxy-α,β-unsaturated ketones having a benzylic hydroxyl group at the δ-position using allyltrimethylsilane mediated by BF3·OEt2, leading to 2,4-diallyl-2-methyl-6-aryltetrahydro-2H-pyran ring systems with quaternary carbon stereogenic centers. This represents the first example of a tandem isomerization followed by one C-O and two C-C bond-forming reactions in one pot. The isolation of TMS-protected lactol as an intermediate from the reaction strongly supports the proposed mechanistic pathway.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
American Chemical Society  
dc.rights
info:eu-repo/semantics/restrictedAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
BF3.OET2 CATALYZED  
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TETRAHYDRO-2H-PYRAN  
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STEREOSELECTIVE SYNTHESIS  
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Química Orgánica  
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Ciencias Químicas  
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CIENCIAS NATURALES Y EXACTAS  
dc.title
BF3·OEt2-Catalyzed Unexpected Stereoselective Formation of 2,4-trans-Diallyl-2-methyl-6-aryltetrahydro-2H-pyrans with Quaternary Stereocenters  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2021-12-03T21:34:12Z  
dc.journal.volume
86  
dc.journal.number
9  
dc.journal.pagination
6518-6527  
dc.journal.pais
Estados Unidos  
dc.journal.ciudad
Washington D. C.  
dc.description.fil
Fil: Srinivas Reddy, D.. Indian Institute of Technology; India  
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Fil: Srinivas, Beduru. Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology; India  
dc.description.fil
Fil: Rachineni, Kavitha. Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology; India  
dc.description.fil
Fil: Jagadeesh, Bharatam. Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology; India  
dc.description.fil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina  
dc.description.fil
Fil: Mohapatra, Debendra K.. Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology; India  
dc.journal.title
Journal of Organic Chemistry  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/acs.joc.1c00352  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/acs.joc.1c00352