Enantioselective Polyene Cyclization via Organo-SOMO Catalysis
نویسندگان
چکیده
منابع مشابه
Enantioselective polyene cyclization via organo-SOMO catalysis.
The first organocatalytic enantioselective radical polycyclization has been accomplished using singly occupied molecular orbital (SOMO) catalysis. The presented strategy relies on a selective single-electron oxidation of chiral enamines formed by condensation of polyenals with an imidazolidinone catalyst employing a suitable copper(II) oxidant. The reaction proceeds under mildly acidic conditio...
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A new strategy for organocatalysis based on the biochemical blueprints of biosynthesis has enabled a new laboratory approach to cascade catalysis. Imidazolidinone-based catalytic cycles, involving iminium and enamine activation, have been successfully combined to allow a large diversity of nucleophiles (furans, thiophenes, indoles, butenolides, hydride sources, tertiary amino lactone equivalent...
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...
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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...
متن کاملA remarkably simple α-oximation of aldehydes via organo-SOMO catalysis.
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.
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2010
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja100185p