Chinese Journal of Organic Chemistry >
Advances of Chiral Spiro Skeleton-Based Bisnitrogen Ligands in Transition-Metal Catalysis
Received date: 2022-10-12
Revised date: 2022-10-20
Online published: 2022-10-25
Chiral spiro skeletons are recognized as a class of “privileged structures” of ligands. Studies toward these spiro ligands have significantly advanced the field of asymmetric catalysis. Bisnitrogen ligands bearing chiral spiro skeletons are reviewed and categorized according to the type of spirocyclic skeletons, including spiro[4.4]nonane-based bis(isoxazoline) ligands (SPRIX), spirobiindane-based bis(oxazoline) ligands (SpiroBox), spirobi(chroman)-based bis(amine) or bis(oxazoline) ligands (SPANamine or SPANBox), and spirocyclic pyrrolidine oxazoline ligands (SPDO). The synthesis and application of these four types of ligands and their applications in transition-metal catalysis are discussed in detail. Compared with the powerful and widely utilized chiral sprio phosphine ligands, the availability and application of spiro bisnitrogen ligands are relatively limited. Nevertheless, their features such as stability under acidic conditions and/or in the presence of an oxidant, superior capability of catalyzing carbene insertion into heteroatom-hydrogen bonds, provide insights and inspirations to the development of novel catalytic systems in asymmetric synthesis.
Xudong Hu , Xinliang Zhang , Wenbo Liu . Advances of Chiral Spiro Skeleton-Based Bisnitrogen Ligands in Transition-Metal Catalysis[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3102 -3117 . DOI: 10.6023/cjoc202210010
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