Enantioselective Organocatalytic Aminomethylation of Aldehydes: A Role for Ionic Interactions and Efficient Access to β2‐Amino Acids.
摘要：
Organocatalytic Mannich addition of aldehydes to a formaldehyde-derived iminium species catalyzed by proline-derived chiral pyrrolidines provides beta-amino aldehydes with >/=90% ee. Mechanistic analysis of the proline-catalyzed reactions suggests that non-hydrogen-bonded ionic interactions at the Mannich reaction transition state can influence stereochemical outcome. The beta-amino aldehydes from our process bear a substituent adjacent to the carbonyl and can be efficiently converted to protected beta2-amino acids, which are important building blocks for beta-peptide foldamers that display useful biological activities.
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关键词：
amino alcohols (acyclic compounds diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism
DOI：
10.1021/ja061731n
被引量：
年份：
2006
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