Highly γ-Regioselective 1,2-Addition of α,β-Unsaturated Oxime Ethers with Allylzinc Bromides: A Straightforward Approach for the Synthesis of Homoallylic Amines

Bo Yang; Songlin Zhang

doi:10.1055/s-0039-1690127

Synthesis, Table of Contents

Synthesis 2019; 51(19): 3736-3746
DOI: 10.1055/s-0039-1690127

paper

Highly γ-Regioselective 1,2-Addition of α,β-Unsaturated Oxime Ethers with Allylzinc Bromides: A Straightforward Approach for the Synthesis of Homoallylic Amines

Authors

Bo Yang
Songlin Zhang∗

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China Email: zhangsl@suda.edu.cn

Abstract

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Abstract

A highly regioselective reaction between allylzinc bromide reagents and α,β-unsaturated oxime ethers for the one-step synthesis of the homoallylic amines is reported. This process is a regioselective 1,2-addition reaction providing a new γ-position with carbon–carbon bond formation. Furthermore, the reaction substrates are widely applicable and can be produced in a high yield.

Key words

regioselectivity - homoallylic amine - α,β-unsaturated oxime ether - organozinc reagent - 1,2-addition

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References

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