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A general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles.

ABSTRACT: A catalytic diastereoselective aldol reaction has been developed for N1-arylated/C2-O-silylated/C3-methylated and brominated/C4-O-methylated pyrroles in its reactions with various aldehydes. Syn adducts emerge with regard to the vicinal nitrogen and oxygen heteroatom substituents. The N1-aryl residue undergoes oxidative cleavage, and the C3-bromine atom undergoes palladium-mediated coupling reactions, both without disturbing the newly created stereocenters.

SUBMITTER: David JG 

PROVIDER: S-EPMC4156244 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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A general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles.

David Jonathan G JG   Bai Wen-Ju WJ   Weaver Marisa G MG   Pettus Thomas R R TR  

Organic letters 20140813 17

A catalytic diastereoselective aldol reaction has been developed for N1-arylated/C2-O-silylated/C3-methylated and brominated/C4-O-methylated pyrroles in its reactions with various aldehydes. Syn adducts emerge with regard to the vicinal nitrogen and oxygen heteroatom substituents. The N1-aryl residue undergoes oxidative cleavage, and the C3-bromine atom undergoes palladium-mediated coupling reactions, both without disturbing the newly created stereocenters. ...[more]

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