α-Azido aldehydes are versatile synthetic intermediates, useful in the construction of α-amino acids, β-amino alcohols, and related compounds. However, catalytic asymmetric methods for their synthesis are lacking.  Instead, these compounds are generally obtained from chiral pool materials such as amino acids, limiting the range of readily available structures.  An alternative approach employing nucleophilic addition of azide to enantiomerically-enriched sulfonyl epoxides will be presented.  The challenges and scope of this reaction will be discussed, focusing on the effects of solvent choice and reaction time on both yield and enantiomeric excess.  Results involving interception of the α-azido aldehyde intermediates with allyltrimethylsilanes to synthesize unsaturated β-azido alcohols will also be presented.  Finally, enantioselective synthesis of the requisite sulfonyl epoxide starting materials using phase transfer-catalyzed Darzens reactions will be disclosed.<br/>

Asymmetric synthesis of enolizable alpha-azido aldehydes from sulfonyl epoxides: Challenges and opportunities

2019 Spring National Meeting

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