Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines

Abstract

Metal-catalyzed reductive coupling has emerged as an alternative to the use of stoichiometric organometallic reagents in an increasingly diverse range of carbonyl and imine additions. In this review, the use of diene, allene, and enyne pronucleophiles in intermolecular carbonyl and imine reductive couplings are surveyed, along with related hydrogen autotransfer processes.

Enantio‐ and Diastereoselective Synthesis of Homopropargyl Amines by Copper‐Catalyzed Coupling of Imines, 1,3‐Enynes, and Diborons

“…We and others have described efficient routes to amines through the multicomponent coupling of imines with hydrocarbon pro‐nucleophiles and boron reagents . Krische pioneered the use of enynes as hydrocarbon pro‐nucleophiles in transition metal‐catalyzed transformations, however, in both reductive and borylative coupling, the asymmetric union of imines and enynes remains an unmet challenge…”

Eine flexible Kupplung von Aldehyden und Alkenen ermöglicht die diastereo‐ und enantioselektive Herstellung von Stereotriaden

“…[1][2][3] Bisherige Routen zur Herstellung dieser Grundgerüste bençtigen aufwendige Reagenzien und mehrstufige Sequenzen, was die Synthese solcher Verbindungen deutlich verlängert. [1][2][3] Bisherige Routen zur Herstellung dieser Grundgerüste bençtigen aufwendige Reagenzien und mehrstufige Sequenzen, was die Synthese solcher Verbindungen deutlich verlängert.…”

Feedstock Reagents in Metal‐Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target‐Oriented Synthesis

“…[8][9][10] These processes enable carbonyl addition from p-unsaturated pronucleophiles,bypassing the use of premetalated reagents and the attendant issues of safety, selectivity,a nd waste posed by their use.T he terminal reductants utilized in these reactions are abundant, lowmolecular-weight feedstocks (elemental hydrogen, 2-propanol and formic acid). [8][9][10] These processes enable carbonyl addition from p-unsaturated pronucleophiles,bypassing the use of premetalated reagents and the attendant issues of safety, selectivity,a nd waste posed by their use.T he terminal reductants utilized in these reactions are abundant, lowmolecular-weight feedstocks (elemental hydrogen, 2-propanol and formic acid).…”