Aminative Umpolung of Aldehydes to α-Amino Anion Equivalents for Pd-Catalyzed Allylation: An Efficient Synthesis of Homoallylic Amines
Organic Letters2014Vol. 16(3), pp. 720–723
Citations Over TimeTop 14% of 2014 papers
Abstract
An attractive strategy for generation of α-amino anions from aldehydes with applications in synthesis of homoallylic amines is described. Aromatic aldehydes can be converted to α-amino anion equivalents via amination with 2,2-diphenylglycine and subsequent decarboxylation. The in situ generated α-imino anions are highly reactive for Pd-catalyzed allylation, forming the corresponding homoallylic amines in high yields with excellent regioselectivity.
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