Journal
ORGANIC LETTERS
Volume 11, Issue 15, Pages 3202-3205Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol9010932
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Funding
- The ACS Petroleum Research Fund [5001009]
- Boston College
- NSF [DBI-0619576]
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Over a century ago, the first reactions of diazomethane with aldehydes delivered methyl ketones. In the interim, aldehydes have been homologated with trimethylsilyldiazomethane, diazoacetates, and aryidiazomethanes, on rare occasion with catalysis, This work describes a mild procedure for convergent ketone assembly from nonstabilized diazoalkanes, including examples of chiral ketone synthesis with disubstituted (internal) nucleophiles, The method's remarkable tolerance to steric crowding is showcased in a simple approach to achyrofuran, a complex dibenzofuran.
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