Journal
ORGANIC LETTERS
Volume 22, Issue 24, Pages 9484-9489Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03461
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We report a DNA-compatible photoredox decarboxylative coupling of alpha-amino acids with carbonyl compounds to access DNA-encoded sp(3)-rich 1,2-amino alcohols. The reaction proceeds efficiently for a wide range of DNA-conjugated aldehydes and ketones and provides the desired 1,2-amino alcohols with conversions generally >50%. Additional utility of the developed protocol is demonstrated by one-pot cyclization of DNA-conjugated 1,2-amino alcohols into oxazolidiones and morpholinones. Lastly, qPCR and sequencing data analysis indicates no significant DNA damage upon photoredox decarboxylative coupling.
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