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Benzylation of Imines with Activated Boronate Nucleophiles.

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.

SUBMITTER: Hollerbach MR

PROVIDER: S-EPMC7041905 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Benzylation of Imines with Activated Boronate Nucleophiles.

Hollerbach Michael R MR Hayes Jacob C JC Barker Timothy J TJ

European journal of organic chemistry 20190121 7

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 o ...[more]

PMID: 32099525

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