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  • Synthesis of unsaturated seven-membered ring lactams through palladium-catalyzed amination and intramolecular cyclocarbonylation reactions of amines and Baylis-Hillman acetates.

Synthesis of unsaturated seven-membered ring lactams through palladium-catalyzed amination and intramolecular cyclocarbonylation reactions of amines and Baylis-Hillman acetates.

Organic letters (2010-12-02)
Hong Cao, Tiago O Vieira, Howard Alper
ABSTRACT

A versatile synthesis of unsaturated seven-membered ring lactams has been developed. The sequence involves hydroamination of Baylis-Hillman acetate with amines, followed by intramolecular cyclocarbonylation reactions of the resulting allylamines. This process can tolerate a wide array of functional groups, and affords lactams in excellent yields.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzylamine, ReagentPlus®, 99%
Sigma-Aldrich
Benzylamine, purified by redistillation, ≥99.5%
Sigma-Aldrich
Benzylamine hydrochloride
Supelco
Benzylamine, for GC derivatization, LiChropur, ≥99.0%