Issue 13, 2023

Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines

Abstract

The one-pot reaction of a chiral aldehyde, p-methoxyaniline or p-fluoroaniline, and triethylborane produces the corresponding alkylated chiral amine with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom in the α-position to the aldehyde. In the case of alkylation of imines derived from chiral aliphatic amines, good yields and moderate to high diastereoselectivity are obtained: yields are significantly better when the preformed imine is used in the reaction with triethyl borane, and diastereoselectivity of the reactions largely depends on the structure of the chiral aliphatic amine. The methodology is successfully applied to the synthesis of romneine, a natural benzylisoquinoline.

Graphical abstract: Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines

Supplementary files

Article information

Article type
Paper
Submitted
01 Mar 2023
Accepted
13 Mar 2023
First published
17 Mar 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 8976-8984

Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines

D. Fuentes-Ríos, C. Muñoz, A. Díaz, F. Sarabia and J. M. López-Romero, RSC Adv., 2023, 13, 8976 DOI: 10.1039/D3RA01397A

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