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Abstract
The use of Rh catalysts derived from a phospholane‐phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N‐CBz‐2‐3‐dehydro‐4‐piperidone, or the coupling of poorly reactive 2‐furyl boronic acids at ambient or near temperatures.
Highlights
The last two decades have seen great advances in enantioselective conjugate additions of aryl boronic acids
Since this is quite an important catalytic reaction, there are many other catalysts that have been designed and tested.[1b]. Fluorinated BINAP analogues have been shown to allow lower catalyst loadings to be used than the Rh/ BINAP system, and more practical conditions for one substrate studied here.[3]
Non-C2-symmetric Phosphine-alkene ligands,[5] phosphine-amide ligands,[6] phosphine-sulfoxide[7] and phosphine-NHC ligands[8] have all been examined in Rh catalyzed conjugate additions of important but generally unproblematic substrates and for novel target synthesis.[1c]. The diversity of ligands studied in these reactions is large, but no phosphinephosphite ligands seem to have been studied in this reaction far.[4]
Summary
The last two decades have seen great advances in enantioselective conjugate additions of aryl (or alkenyl) boronic acids. These reactions have received significant attention, and are a useful tool for the asymmetric synthesis of quite a wide variety of target molecules.[1] There are quite a range of different catalysts that have been developed and shown to be effective from the perspective of promoting highly enantioselective coupling reactions (Scheme 1).
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