Enantioselective Synthesis of α‑Oxy Amides via Umpolung Amide Synthesis

α-Oxy amides are prepared through enantioselective synthesis using a sequence beginning with a Henry addition of bromonitromethane to aldehydes and finishing with Umpolung Amide Synthesis (UmAS). Key to high enantioselection is the finding that ortho-iodo benzoic acid salts of the chiral copper­(II)...

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Published inJournal of the American Chemical Society Vol. 134; no. 37; pp. 15233 - 15236
Main Authors Leighty, Matthew W, Shen, Bo, Johnston, Jeffrey N
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.09.2012
Amer Chemical Soc
Subjects
Amides - chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Stereoisomerism
HENRY NITROALDOL REACTION
ACID-DERIVATIVES
(S)-MANDELIC ACID
KETONES
DIMETHYLZINC
HYDROXY
COMPLEXES
KETOESTERS
ASYMMETRIC HYDROGENATION
HIGHLY EFFICIENT CATALYSTS
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Summary:α-Oxy amides are prepared through enantioselective synthesis using a sequence beginning with a Henry addition of bromonitromethane to aldehydes and finishing with Umpolung Amide Synthesis (UmAS). Key to high enantioselection is the finding that ortho-iodo benzoic acid salts of the chiral copper­(II) bis­(oxazoline) catalyst deliver both diastereomers of the Henry adduct with high enantiomeric excess, homochiral at the oxygen-bearing carbon. Overall, this approach to α-oxy amides provides an innovative complement to alternatives that focus almost entirely on the enantioselective synthesis of α-oxy carboxylic acids.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja306225u