Diverse Alkanones by Catalytic Carbon Insertion into the Formyl C−H Bond. Concise Access to the Natural Precursor of Achyrofuran

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 aryldiazomethanes, on rare occasion with catalysis. This work describes a mild procedure for convergent...

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Veröffentlicht in:	Organic letters 2009-08, Vol.11 (15), p.3202-3205
Hauptverfasser:	Wommack, Andrew J, Moebius, David C, Travis, Austin L, Kingsbury, Jason S
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbon - chemistry Catalysis Diabetes Mellitus, Type 2 - drug therapy Drug Design Furans - chemical synthesis Furans - chemistry Hypoglycemic Agents - chemical synthesis Hypoglycemic Agents - chemistry Ketones - chemistry
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creator	Wommack, Andrew J Moebius, David C Travis, Austin L Kingsbury, Jason S
description	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 aryldiazomethanes, 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.
doi_str_mv	10.1021/ol9010932
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subjects	Carbon - chemistry Catalysis Diabetes Mellitus, Type 2 - drug therapy Drug Design Furans - chemical synthesis Furans - chemistry Hypoglycemic Agents - chemical synthesis Hypoglycemic Agents - chemistry Ketones - chemistry
title	Diverse Alkanones by Catalytic Carbon Insertion into the Formyl C−H Bond. Concise Access to the Natural Precursor of Achyrofuran
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