Catalytic Enantioselective Reaction of Allenylnitriles with Imines Using Chiral Bis(imidazoline)s Palladium(II) Pincer Complexes

Chiral dienes are important ligands in asymmetric catalysis but they are less accessible than other commonly used ligands such as chiral bisphosphines. Here, we show that intramolecular [4 + 2] cycloaddition of a simply attained chiral allenecarboxanilide readily affords pseudoenantiomeric bicyclo[2.2.2]octa-2,5dienes containing an alkenyl bromide, which can be readily functionalized to give diverse chiral diene ligands. The synthesis is straightforward and easily conducted on multigram scales. These ligands exhibit high performance in nine types of enantioselective Rh(I)-catalyzed 1,4-addition or 1,2-addition reactions.

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Organocatalytic Asymmetric C(sp²)−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates

Shi

Zheng

et al. 2020

Angewandte Chemie

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Herein we describe the first organocatalytic asymmetric C(sp2)−H allylation of racemic trisubstituted allenoates with Morita–Baylis–Hillman (MBH) carbonates to access axially chiral tetrasubstituted allenoates. Various trisubstituted allenoates and MBH carbonates were well tolerated under mild reaction conditions, providing novel chiral tetrasubstituted allenoates with adjacent axial chirality and tertiary carbon stereocenters in high yields with good to excellent diastereoselectivities and enantioselectivities.

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Catalytic Enantioselective Reaction of Allenylnitriles with Imines Using Chiral Bis(imidazoline)s Palladium(II) Pincer Complexes

Cited by 8 publications

References 75 publications

Enantioselective Allenylation of Ketimines Derived from Isatins Using Chiral Bis(imidazoline)‐Palladium Catalysts

Enantioselective Allenylation of Ketimines Derived from Isatins Using Chiral Bis(imidazoline)‐Palladium Catalysts

A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis

Organocatalytic Asymmetric C(sp²)−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates

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Catalytic Enantioselective Reaction of Allenylnitriles with Imines Using Chiral Bis(imidazoline)s Palladium(II) Pincer Complexes

Cited by 8 publications

References 75 publications

Enantioselective Allenylation of Ketimines Derived from Isatins Using Chiral Bis(imidazoline)‐Palladium Catalysts

Enantioselective Allenylation of Ketimines Derived from Isatins Using Chiral Bis(imidazoline)‐Palladium Catalysts

A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis

Organocatalytic Asymmetric C(sp2)−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates

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Product

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Organocatalytic Asymmetric C(sp²)−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates