83520-78-9Relevant articles and documents
Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation
Palmer, W. Neil,Zarate, Cayetana,Chirik, Paul J.
, p. 2589 - 2592 (2017)
A highly diastereoselective carbon-carbon bond-forming reaction involving the tandem coupling of benzyltriboronates, enoates, and alkyl halides is described. This method was enabled by the discovery of α-diimine nickel catalysts that promote the chemosele
Nazarov cyclization of divinyl ketones bearing an ester group at the β-position: A remarkable effect of α-substitution and alkene geometry on regioselectivity
Sudhakar, Gangarajula,Raghavaiah, Jakka,Mahesh, Gaddam,Singarapu, Kiran Kumar
, p. 2866 - 2872 (2016/03/12)
The Nazarov cyclization of divinyl ketones with an ester at the β-position was examined with particular reference to where the cyclic double bond forms. We observed unprecedented regioselectivity, dictated by the subtle substitution patterns at the α-position and alkene geometry of α,β and mostly, this selectivity is regardless of substitutions at α′- and β′-positions. The major implications of these observations are an aromatic group at the α-position with E-olefin geometry provides a cyclopentenone in which the double bond is not in conjugation with an ester, whereas Z-olefin provides a cyclopentenone in which the double bond is in conjugation with an ester; and divinyl ketones bearing an ester group at the β-position and an alkyl group at the α-position with E-olefin geometry provide a cyclopentenone in which the double bond is in conjugation with the ester.
Nazarov cyclization of divinyl and arylvinyl epoxides: Application in the synthesis of resveratrol-based natural products
Sudhakar, Gangarajula,Satish, Kovela
, p. 6475 - 6480 (2015/04/22)
New variation in the Nazarov cyclization has been developed by preparing divinyl and arylvinyl epoxides as pentadienyl cation precursors for the first time. Highly substituted cyclopentadienes, hydrindienes, and indenes were synthesized to demonstrate the compatibility of this reaction with substrates bearing a variety of substitutions and having different types of epoxides. Application of this method in the synthesis of resveratrol-based natural products was also demonstrated.
Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); A new 'metal free' life for the Rupe rearrangement
Nandi, Ganesh C.,Rathman, Benjamin M.,Laali, Kenneth K.
supporting information, p. 6258 - 6263 (2013/10/22)
A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Br?nsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.
Hydroacylation of 2-butyne from the alcohol or aldehyde oxidation level via ruthenium catalyzed C-C bond forming transfer hydrogenation
Williams, Vanessa M.,Leung, Joyce C.,Patman, Ryan L.,Krische, Michael J.
supporting information; experimental part, p. 5024 - 5029 (2009/10/24)
Under the conditions of ruthenium catalyzed transfer hydrogenation, 2-butyne couples to alcohols 1a-1j to deliver α,β-unsaturated ketones 3a-3j in good to excellent isolated yields with complete E-stereoselectivity. Under identical conditions, aldehydes 2
Carbon-carbon bond forming reactions of η3-allyl iron tricarbonyl anions with carbon electrophiles
Chang, Seok,Yoon, Jaeyon,Brookbart, Maurice
, p. 1869 - 1879 (2007/10/02)
Reaction of the η3-allyl iron tricarbonyl anion, 1, with alkyl halides (RX, R = -CH3, -CH2Ph, -(CH2)3CH3, -CH(CH3)2,-CH2CH=CH2) followed by treat
