Setembro 2013 vol. 1 num. 1 - Brazilian Meeting on Organic Synthesis 2011

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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.

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Palavras-chave: aldol reactions, boron enolate, 1, 5-stereoinduction,

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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, 201
  • [2] 2 Kobayashi, Y.; Tan, C.-H.; Kishi, Y. Helv. Chim. Acta 2000, 83, 256
Como citar:

Polo, Ellen Christine; Dias, Luiz Carlos; "Boron-mediated aldol reactions of a methyl ketone containing a cyclic silicon protecting group", p. 87 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-14bmos-R0087-1

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