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Sequential Reactions Promoted by Manganese: Completely Stereoselective Synthesis of (E)-α,β-Unsaturated Amides, Ketones, Aldehydes, and Carboxylic Acids‡
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Abstract
A complete E-selective synthesis of α,β-unsaturated amides through a sequential reaction of a range of dichloroamides with a variety of aldehydes promoted by Rieke manganese (Mn*) is reported. A mechanism based on a sequential aldol-type reaction and a completely stereoselective β-elimination is proposed to explain these results. The unsaturated amides obtained are readily and efficiently transformed into α,β-unsaturated ketones, aldehydes, or carboxylic acids without loss of the diastereoisomeric purity of the C−C double bond.
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
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Stereocontrolled Synthesis of Z-Dienes via an Unexpected Pericyclic Cascade Rearrangement of 5-Amino-2,4-pentadienals
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Sarah E. Steinhardt, Joel S. Silverston and Christopher D. VanderwalJournal of the American Chemical Society2008 130 (24), 7560-7561Donor−acceptor dienes known as Zincke aldehydes, which derive readily from the ring-opening reactions of pyridinium salts with secondary amines, undergo a fascinating thermal rearrangement reaction to afford Z-α,β,γ,δ-unsaturated amides with excellent ...
Stereospecific and Stereoselective Alkyl and Silylcyclopropanation of α,β-Unsaturated Amides
José M. Concellón, Humberto Rodríguez-Solla, Carmen Méjica, Elena G. Blanco, Santiago García-Granda, and M. Rosario DíazOrganic Letters2008 10 (2), 349-352Stereospecific and Stereoselective Alkyl and Silylcyclopropanation of α,β-Unsaturated Amides
José M. Concellón, Humberto Rodríguez-Solla, Carmen Méjica, Elena G. Blanco, Santiago García-Granda, and M. Rosario DíazOrganic Letters2008 10 (2), 349-352A novel chromium-promoted alkyl- and silyl cyclopropanation of (E)- or (Z)-,-unsaturated amides in which the CC double bond is di-, or trisubstituted is described. This process takes place with total stereospecificity, and the new stereogenic center is ...
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History
- Published In Issue October 12, 2007
- Received June 29, 2007
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