Boron-mediated aldol reactions of a methyl ketone containing a cyclic silicon protecting group

Boron-mediated aldol reactions of a methyl ketone containing a cyclic silicon protecting group

Polo, Ellen Christine; Dias, Luiz Carlos

Abstract:

We have showed that aldol reactions involving boron enolates of methyl ketone containing a trans acetonide 1 with achiral aldehydes provided the corresponding aldol adducts with moderate to good levels of diastereoselectivity, favoring the 1,5-anti adduct. In this work we report the use of the boron enolate generated from methyl ketone 8, containing a cyclic silicon protecting group in a trans relationship in aldol reactions with achiral aldehydes. Our intention is to evaluate the steric and eletronic effect of the silicon protecting group in the selectivity of the reactions.

We have showed that aldol reactions involving boron enolates of methyl ketone containing a trans acetonide 1 with achiral aldehydes provided the corresponding aldol adducts with moderate to good levels of diastereoselectivity, favoring the 1,5-anti adduct. In this work we report the use of the boron enolate generated from methyl ketone 8, containing a cyclic silicon protecting group in a trans relationship in aldol reactions with achiral aldehydes. Our intention is to evaluate the steric and eletronic effect of the silicon protecting group in the selectivity of the reactions.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0087-1

Referências bibliográficas

• [1] 1 Polo, E. C. “Controle da estereoquímica remota 1,5 em adições de enolatos de boro de metilcetonas a aldeídos”; Dissertação de Mestrado, UNICAMP, 2011.
• [2] 2 Kobayashi, Y.; Tan, C.-H.; Kishi, Y. Helv. Chim. Acta 2000, 83, 2562.

Como citar:

Polo, Ellen Christine; Dias, Luiz Carlos; "Boron-mediated aldol reactions of a methyl ketone containing a cyclic silicon protecting group", p-87-87. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0087-1