The C2-symmetric bis(oxazoline) copper(II) complex proves to be an excellent catalyst in the Friedel-Crafts alkylation of indoles with alpha'-phosphoric enones. The enantioselectivities of this reaction are obtained in up to 98% ee.
Using the C 2 -symmetric bis-oxazoline copper(II) catalyst 6f as a chiral Lewis acid, a'-phosphoric enones 2 undergo 1,3-dipolar cycloaddition with nitrones 3 to provide isoxazolidines 4 with very high enantioselectivity and endo/exo selectivity.
Radical acylations to prepare carbonyl compounds are described and focus on indirect acylation approaches using sulfonyl oxime ethers under tin-mediated and tin-free conditions. The efficiency of carboxylic acid derivatives as carbonyl group radical acceptors in radical acylation and carboxylation reactions is discussed.
The b-elimination of an organophosphoryl group from an iminyl radical is observed for the first time. On the basis of this finding, radical cyanation of alkyl iodides is achieved by using diethylphosphoryl cyanide.
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