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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 14
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Synthetic Communications Review

Preparation of bicyclic β-lactam and bicyclic 1,3-oxazinone scaffolds using combined cycloaddition and metathesis processes

, &
Pages 1793-1804 | Received 01 Mar 2018, Published online: 11 Jun 2018
 

Abstract

A simple, efficient two-step method for the preparation of heterobicyclic compounds was developed. Starting from 5-acyl or 5-carbamoyl-2,2-dimethyl-1,3-dioxa-4,5-dione bicyclic scaffolds of 1-azabicyclo[5.2.0]non-3-en-9-one, 6,9,10,10a-tetrahydro-4H-[1,3]oxazino[3,2-a]azepin-4-one, and 6,9,10,10a-tetrahydro-2H-[1,3]oxazino[3,2-a]azepine-2,4(3H)-dione were prepared using cycloaddition of thermally generated ketenes to aldimines with unsaturated side chains, followed by metathesis. The method was applied to ring closing metathesis (RCM) of different heterocyclic substrates to demonstrate its versatility.

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