Enantio- and E-selective Carbonyl-Ene Cyclization of 5-Substituted 5-Hexenals Catalyzed by Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acids.
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DOI: 10.1021/acs.orglett.5c02136
Abstract: The enantio- and E-selective carbonyl-ene cyclization (6-endo-trig) of 5-substituted 5-hexanals has been achieved using a new Lewis-acid-assisted chiral Brønsted acid (LBA), i.e., a tris(pentafluorophenyl)borane-chiral phosphoric acid complex. The high enantioselectivity and E-selectivity are induced through… read more here.
Keywords: enantio selective; tris pentafluorophenyl; ene cyclization; carbonyl ene ... See more keywords
Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction.
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DOI: 10.1021/acs.orglett.7b01329
Abstract: An efficient desymmetrizing carbonyl-ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N'-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol methodology originates… read more here.
Keywords: carbonyl ene; desymmetrizing carbonyl; distant stereocenters; ene reaction ... See more keywords
F10BINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc03587c
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DOI: 10.1039/c8sc03587c
Abstract: An enantioselective carbonyl-ene reaction of 1,1-disubstituted olefins with ethyl glyoxylate was accomplished using an F10BINOL-derived chiral phosphoric acid of which the perfluoro-binaphthyl skeleton is beneficial not only for adopting high catalytic activity but also for… read more here.
Keywords: carbonyl ene; f10binol derived; derived chiral; chiral phosphoric ... See more keywords
Fe(BF4)2 catalyzed inter- and intramolecular carbonyl-ene reaction of trifluoropyruvate
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DOI: 10.1055/s-0036-1591858
Abstract: Inter- and intramolecular carbonyl-ene reactions have been developed using 5 mol% Fe(BF 4 ) 2 as catalyst, affording homoallylic alcohols in 36–87% isolated yields. This catalyst, prepared from FeCl 2 and AgBF 4 , is… read more here.
Keywords: carbonyl ene; intramolecular carbonyl; ene; ene reaction ... See more keywords