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Stereoselective NH Insertion‐Arylation Reactions of Nitrodiazoesters
Author(s) -
So Sonia S.,
Mattson Anita E.
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300285
Subject(s) - chemistry , umpolung , phosphoric acid , nucleophile , stereoselectivity , yield (engineering) , catalysis , glycine , organocatalysis , organic chemistry , combinatorial chemistry , enantioselective synthesis , amino acid , biochemistry , materials science , metallurgy
Phosphoric acid derivatives operate as effective catalysts for the synthesis of glycines in high yield through multicomponent coupling reactions of nitrodiazoesters, anilines, and indoles. This interesting process requires double polarity reversal, or umpolung, of the ester functionality: two nucleophiles undergo addition to the carbon alpha to an ester. Modest control over the absolute stereochemistry of the glycine products is attainable under the influence of chiral BINOL‐based phosphoric‐acid‐derived catalysis.