Abstract
A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high‐value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units.
Highlights
A highly enantio- and diastereoselective coppercatalyzed three-component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials
Enriched homoallylic amines are keystone building blocks, crucial to the production of many important compounds, such as pharmaceuticals, natural products, catalysts, and ligands.[1]. They are synthesized by the treatment of imines with allyl metal reagents or metalloids under reagent or substrate control, which provides homoallylic amines with magnificent stereoselectivity (Scheme 1 A).[2]
To keep apace with the demands of modern synthetic chemistry, multicomponent reactions must address challenging couplings in which numerous stereocenters are installed selectively:[8] If complex chiral products could be assembled from several readily available achiral components in a onepot process, diverse collections of high-value compounds could be quickly constructed by simple variation of the material inputs
Summary
A highly enantio- and diastereoselective coppercatalyzed three-component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. Important homoallylic amines from the enantioselective allylation of imines.
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