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The Effect of β-Substituents in Aldol Reactions of Boron Enolates

Lucas Danilo Dias, Emilio Carlos de Lucca Júnior, Marli Ferreira, D. Garcia, Cássio Antônio Tormena

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Abstract

Significance Traditional aldol reactions of boron enolates yield 1,5- anti diastereomers; forming the 1,5- syn diastereomer has proven to be challenging. This report describes that both PMB and TBS protecting groups of β- tert -butyl methyl ketones will result in 1,5- syn stereocontrol when reacting with an achiral aldehyde. These outcomes can be explained by theoretical calculations of transition states.

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What this paper is about

Significance Traditional aldol reactions of boron enolates yield 1,5- anti diastereomers; forming the 1,5- syn diastereomer has proven to be challenging. This report describes that both PMB and TBS protecting groups of β- tert -butyl methyl ketones will result in 1,5- syn stereocontrol when reacting with an achiral aldehyde. These outcomes can be explained by theoretical calculations of transition states.

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Available abstract

Significance Traditional aldol reactions of boron enolates yield 1,5- anti diastereomers; forming the 1,5- syn diastereomer has proven to be challenging. This report describes that both PMB and TBS protecting groups of β- tert -butyl methyl ketones will result in 1,5- syn stereocontrol when reacting with an achiral aldehyde. These outcomes can be explained by theoretical calculations of transition states.

Key concepts: Aldol reaction, Diastereomer, Chemistry, Boron, Yield (engineering), Aldehyde, Organic chemistry, Medicinal chemistry

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