A remarkably simple α-oximation of aldehydes via organo-SOMO catalysis.
نویسندگان
چکیده
A novel α-oximation reaction of unactivated aldehydes has been achieved in excellent yields by reaction with NaNO(2)-FeCl(3) couple and in the presence of pyrrolidine as organocatalyst.
منابع مشابه
The Intramolecular Asymmetric Allylation of Aldehydes via Organo-SOMO Catalysis: A Novel Approach to Ring Construction.
The intramolecular asymmetric cyclization of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3π-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective cyclization with an ar...
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A critical objective for the continued advancement of the field of asymmetric catalysis is the design and implementation of novel activation modes that allow the invention of unprecedented transformations. Recently, our laboratory introduced a new mode of organocatalytic activation, termed (singly occupied molecular orbital) SOMO catalysis, that is founded upon the transient production of a 3π-...
متن کاملEnantioselective alpha-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway.
The intramolecular alpha-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3pi-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective reaction with an array of pe...
متن کاملEnantioselective organo-SOMO cascade cycloadditions: a rapid approach to molecular complexity from simple aldehydes and olefins.
A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes a...
متن کاملNature of intermediates in organo-SOMO catalysis of alpha-arylation of aldehydes.
The intramolecular alpha-arylation of aldehydes via organo-SOMO catalysis was investigated using density functional theory (B3LYP and M06-2X functionals). The geometries, spin densities, Mulliken charges, and molecular orbitals of the reacting enamine radical cations were analyzed, and the nature of the resulting cyclized radical cation intermediates was characterized. In agreement with experim...
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ورودعنوان ژورنال:
- Chemical communications
دوره 48 43 شماره
صفحات -
تاریخ انتشار 2012