BF3·OEt2-Catalyzed Unexpected Stereoselective Formation of 2,4-trans-Diallyl-2-methyl-6-aryltetrahydro-2H-pyrans with Quaternary Stereocenters

Srinivas Reddy, D.; Srinivas, Beduru; Rachineni, Kavitha; Jagadeesh, Bharatam; Sarotti, Ariel Marcelo; Mohapatra, Debendra K.

BF3·OEt2-Catalyzed Unexpected Stereoselective Formation of 2,4-trans-Diallyl-2-methyl-6-aryltetrahydro-2H-pyrans with Quaternary Stereocenters Volver a la Vista simple
dc.conicet.fuente	individual
dc.conicet.organizacion	Indian Institute of Technology
dc.conicet.organizacion	Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology
dc.conicet.organizacion	Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology
dc.conicet.organizacion	Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology
dc.conicet.organizacion	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
dc.conicet.organizacion	Council of Scientific and Industrial Research Ministry of Science and Technology. Indian Institute of Chemical Technology
dc.conicet.paisOrganizacion	India
dc.conicet.paisOrganizacion	India
dc.conicet.paisOrganizacion	India
dc.conicet.paisOrganizacion	India
dc.conicet.paisOrganizacion	Argentina
dc.conicet.paisOrganizacion	India
dc.conicet.produccionid	9637187
dc.contributor.author	Srinivas Reddy, D.
dc.contributor.author	Srinivas, Beduru
dc.contributor.author	Rachineni, Kavitha
dc.contributor.author	Jagadeesh, Bharatam
dc.contributor.author	Sarotti, Ariel Marcelo
dc.contributor.author	Mohapatra, Debendra K.
dc.date.accessioned	2021-12-22T16:56:39Z
dc.date.available	2021-12-22T16:56:39Z
dc.date.issued	2021-05
dc.date.updated	2021-12-03T21:34:12Z
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.	es
dc.description.fil	Fil: Srinivas Reddy, D.. Indian Institute of Technology; India
dc.description.fil	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.format	application/pdf	es
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	es
dc.identifier.institucional	CONICET
dc.identifier.issn	0022-3263	es
dc.identifier.repo	CONICET Digital
dc.identifier.uri	http://hdl.handle.net/11336/149200
dc.journal.ciudad	Washington D. C.	es
dc.journal.number	9	es
dc.journal.pagination	6518-6527	es
dc.journal.pais	Estados Unidos	es
dc.journal.title	Journal of Organic Chemistry	es
dc.journal.volume	86	es
dc.language.iso	eng	es
dc.publisher	American Chemical Society	es
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
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	es
dc.subject	TETRAHYDRO-2H-PYRAN	es
dc.subject	STEREOSELECTIVE SYNTHESIS	es
dc.subject.classification	Química Orgánica	es
dc.subject.classification	Ciencias Químicas	es
dc.subject.classification	CIENCIAS NATURALES Y EXACTAS	es
dc.title	BF3·OEt2-Catalyzed Unexpected Stereoselective Formation of 2,4-trans-Diallyl-2-methyl-6-aryltetrahydro-2H-pyrans with Quaternary Stereocenters	es
dc.type	info:eu-repo/semantics/article
dc.type	info:ar-repo/semantics/artículo
dc.type	info:eu-repo/semantics/publishedVersion

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