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Benzylation of Imines With Activated Boronate Nucleophiles

Michael R Hollerbach, Jacob C Hayes, Timothy J Barker

European J Org Chem. 2019 Feb 21;2019(7):1646-1648.

PMID: 32099525

Abstract:

Benzylation reactions of N-tosyl imines and N-tert-butanesulfinyl imines using benzylboronic acid pinacol ester are reported. s-Butyllithium was used to activate the boronic ester, rendering it nucleophilic. The reaction was compatible with electronically diverse substituents on the imine in both substrate classes. Good diastereoselectivity was observed in additions to N-tert-butylsulfinylaldimines. The diastereoselectivity observed in these reactions is consistent with an open transition state for the addition. Examples of a secondary alkylboronic ester nucleophile and an N-tert-butanesulfinyl trifluoromethylketimine electrophile are also included.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP87100285 Benzylboronic acid pinacol ester Benzylboronic acid pinacol ester 87100-28-5 Price
LS793369 N-[2-hydroxyethyl]benzamide-3-boronic acid, pinacol ester N-[2-hydroxyethyl]benzamide-3-boronic acid, pinacol ester Price
LS793381 4-N-Methylcarboxamidophenylboronic acid, pinacol ester 4-N-Methylcarboxamidophenylboronic acid, pinacol ester Price
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