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BIBTEX RIS

1,5-Asymmetric Induction in Boron-Mediated Aldol Reactions of β-Alkoxy Methylketones

2008; American Chemical Society; Volume: 73; Issue: 16 Linguagem: Inglês

10.1021/jo8009165

ISSN

1520-6904

Autores

Luiz C. Dias, Anderson A. de Marchi, Marco A. B. Ferreira, Andrea M. Aguilar,

Tópico(s)

Fluorine in Organic Chemistry

Resumo

Good levels of substrate-controlled, 1,5-syn-stereoinduction are obtained in boron-mediated aldol reactions of β-trichloromethyl-β-alkoxy and β-trifluoromethyl-β-alkoxy methylketones with achiral aldehydes, independent of the nature of the β-alkoxy protecting group (TBS or PMB). In the case of boron aldol reactions of β-aryl-β-alkoxy methylketones, the 1,5-anti-adducts were obtained with high levels of diastereoselectivity only with a β-OPMB group.

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