Highly Anti-Selective One-Pot Multicomponent Synthesis of Mannich-Type N-Acylated β-Amino Acid Derivatives by Copper or Sodium Salt Catalysis

A stereo-defined process has been developed for the synthesis of Mannich-type products using readily available copper sulfate or sodium chloride as catalyst. Good to excellent diastereoselectivity has been achieved for a broad array of substrates. The observed diastereoselectivity is explained on th...

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Bibliographic Details
Published in:Synthetic communications 2012-04, Vol.42 (8), p.1162-1176
Main Authors: Bahulayan, D., Shinu, V. S., Pramitha, P., Arun, S., Sheeja, B.
Format: Article
Language:English
Subjects:
Amido ketone
common salt
Mannich-type
multicomponent reaction
stereoselectivity
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Summary:A stereo-defined process has been developed for the synthesis of Mannich-type products using readily available copper sulfate or sodium chloride as catalyst. Good to excellent diastereoselectivity has been achieved for a broad array of substrates. The observed diastereoselectivity is explained on the basis of the steric interaction between the acyloxy group of the aldehyde carbon and the more hindered α-substituted enolate anion. This steric interaction helps the addition to take place through the less-hindered face to produce the anti-isomers predominantly. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2010.537008