Controle da estereoquímica remota 1,5 em adições de enolatos de boro de metilcetonas a aldeídos / Control of 1,5 remote stereochemistry in additions of boron enolates of methylketones to aldehydes

AUTOR(ES)

Ellen Christine Polo

FONTE

IBICT - Instituto Brasileiro de Informação em Ciência e Tecnologia

DATA DE PUBLICAÇÃO

18/02/2011

RESUMO

The aldol reactions of the boron enolate generated from methylketone 44 (containing a trans-acetonide), led to aldol adducts with moderate to good levels of diastereoselectivity, favoring the 1,5-anti adduct. The aldol reactions involving the boron enolate of methylketone 45 (containing a cis-acetonide) gave the corresponding aldol adducts with excellent levels of diastereoselectivity, favoring the 1,5-anti adduct. The aldol reactions of the boron enolate generated from methylketone 46 (containing a cyclic silicon protecting group and trans relationship between the chiral centers), led to the formation of aldol adducts with moderate to good levels of diastereoselectivity favoring the 1,5-anti isomer. The aldol reaction between the boron enolate prepared from methylketone 47 (containing a cyclic silicon protecting group and cis relationship between the chiral centers), led to the formation of aldol adduct with good level of diastereoselectivity favoring the 1,5-anti isomer.

ASSUNTO(S)

reação aldólica enolato de boro metilcetonas aldol reaction boron enolate methylketone

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