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Enantioselective Synthesis of β-Hydrazino Alcohols Using Alcohols and N-Boc-Hydrazine as Substrates

Zhihao Cui and Da-Ming Du*

*School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, People’s Republic of China, Email: dudmbit.edu.cn

Z. Cui, D.-M. Du, Org. Lett., 2016, 18, 5616-5619.

DOI: 10.1021/acs.orglett.6b02841 (free Supporting Information)


Abstract

In situ aerobic dual oxidation with asymmetric organocatalysis enables an enantioselective synthesis of α-hydrazino aldehydes from alcohols and N-Boc hydrazine instead of the conventional combination of aldehydes with azodicarboxylates. This reaction tolerates various substituents on the alcohol component and features excellent enantiocontrol, cheap starting materials, operational simplicity, and scalability.

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Key Words

hydrazines, TEMPO, oxygen, organocatalysis, sodium borohydride


ID: J54-Y2016