Copper-catalyzed asymmetric 1,2-arylboration of enamines: access to chiral borate-containing 3,3′-disubstituted isoindolinones

Xie, Jia-Qi; Wang, Bing-Xia; Liang, Ren-Xiao; Jia, Yi-Xia

doi:10.1039/d4ob00896k

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00896k

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Copper-catalyzed asymmetric 1,2-arylboration of enamines: access to chiral borate-containing 3,3′-disubstituted isoindolinones

Jia-Qi Xie,

Bing-Xia Wang,

Ren-Xiao Liang

et al.

Abstract: An enantioselective copper-catalyzed 1,2-arylboration reaction of enamines has been developed by employing (R)-xyl-BINAP as a chiral ligand. A number of chiral borate-containing 3,3’-disubstituted isoindolinones are achieved in moderate to good...

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Regio‐ and Diastereoselective One‐pot Double Cascade Hybrid Formation/[3+3] Spirocyclization for the Synthesis of 3‐Spiropiperidines Under Phase Transfer Conditions

Di Mola,

Sadeq Mousavi,

Simeone

et al. 2024

Adv Synth Catal

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Herein, we report an efficient approach to synthesizing hybrid 3‐spiropiperidines heterocycles that incorporate both 3‐isochromanone and 3‐isoindolinone units through a one‐pot, double cascade reaction facilitated by an economical K₂CO₃/TBAB catalytic system. By examining the nucleophilicity of the lactone 3‐isochromanone, we developed a cascade reaction pathway that first generates a bi‐nucleophilic hybrid intermediate, which then undergoes [3+3] spirocyclization with α,β‐unsaturated aldehydes. The regioselectivity of the spirocyclization strongly depends on the substitution pattern of lactam ring. The process exhibits high diastereoselectivity, even with the formation of three or four stereocenters, including two contiguous quaternary carbons. These sequential cascade reactions were successfully scaled up, and the subsequent reactivity was readily analyzed, enabling the transformation of existing functional groups into valuable new functionalities.

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Regio‐ and Diastereoselective One‐pot Double Cascade Hybrid Formation/[3+3] Spirocyclization for the Synthesis of 3‐Spiropiperidines Under Phase Transfer Conditions

Di Mola,

Sadeq Mousavi,

Simeone

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

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Copper-catalyzed asymmetric 1,2-arylboration of enamines: access to chiral borate-containing 3,3′-disubstituted isoindolinones

Abstract: An enantioselective copper-catalyzed 1,2-arylboration reaction of enamines has been developed by employing (R)-xyl-BINAP as a chiral ligand. A number of chiral borate-containing 3,3’-disubstituted isoindolinones are achieved in moderate to good...

Cited by 1 publication

References 60 publications

Regio‐ and Diastereoselective One‐pot Double Cascade Hybrid Formation/[3+3] Spirocyclization for the Synthesis of 3‐Spiropiperidines Under Phase Transfer Conditions

Regio‐ and Diastereoselective One‐pot Double Cascade Hybrid Formation/[3+3] Spirocyclization for the Synthesis of 3‐Spiropiperidines Under Phase Transfer Conditions

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