Synthesis of chiral iodo-N,O-acetonide aminal scaffolds via an efficient cascade reaction of amino acid-derived epoxides |
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Authors: | J Paige SouderZachary M Evans Joshua A DriverEric J Pozzo Andrew J Lampkins |
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Institution: | a Department of Chemistry & Biochemistry, Samford University, 800 Lakeshore Drive, Birmingham, AL 35229, USA b McWhorter School of Pharmacy, Samford University, 800 Lakeshore Drive, Birmingham, AL 35229, USA |
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Abstract: | Novel amino acid-derived iodo-N,O-acetonide aminals were developed as chiral, non-epimerizable scaffolds to facilitate complex molecule synthesis. These scaffolds are readily prepared from commercially available amino acid derivatives in ?6 steps, contain an orthogonally-protected β-hydroxy amine moiety, and feature a directly reactive alkyl-iodide group for facile substitution chemistry. Further, a novel ring opening/cyclization cascade reaction was developed to prepare these compounds efficiently (59-72%) from readily available epoxide derivatives. |
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