1995
DOI: 10.1021/jo00128a039
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Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones

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Cited by 53 publications
(40 citation statements)
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“…Inspired by Portella's success in the synthesis of acyl(allyl)silanes using benzotriazole hemiaminals as umpolung equivalents of aldehydes, 37,57 we adopted a similar synthetic pathway. This strategy, originally developed by Katritzky, 58 benefits from facile late-stage hydrolysis of the hemiaminals to the corresponding carbonyls. Olefin crossmetathesis was performed on intermediate 2a, as the acylsilane moiety seems to inhibit the Grubbs catalyst.…”
Section: Resultsmentioning
confidence: 99%
“…Inspired by Portella's success in the synthesis of acyl(allyl)silanes using benzotriazole hemiaminals as umpolung equivalents of aldehydes, 37,57 we adopted a similar synthetic pathway. This strategy, originally developed by Katritzky, 58 benefits from facile late-stage hydrolysis of the hemiaminals to the corresponding carbonyls. Olefin crossmetathesis was performed on intermediate 2a, as the acylsilane moiety seems to inhibit the Grubbs catalyst.…”
Section: Resultsmentioning
confidence: 99%
“…Lithiated dithioacetals such as 1,3-dithiane 3 are still the most widely used formyl anion equivalents [1c,9] and are complemented by lithiated sulfoxide 4, [10] lithiated or silylated thiazole 5 [11] and benzotriazole 6. [12] Furthermore, these types of formyl anion equivalents can be made chiral as exemplified for lithiated N-Boc-thiazolidine 7 [13] [in the presence of (-)-sparteine], chiral metallated thiazolidine 8a as well as silylthiazolidine 8b [14] and lithiated thiomethyloxazolidinone 9. [15] Figure 1.…”
Section: Formyl Anion Equivalentsmentioning
confidence: 99%
“…Thus, 1-(1-alkoxy-1-arylmethyl)benzotriazoles 60 (available from aromatic aldehydes and benzotriazole with the corresponding alcohol, or trimethyl or triethyl orthoformate) 101 …”
Section: β-Alkoxy Synthons From Alkoxymethylbenzotriazoles and Phenylmentioning
confidence: 99%