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Catalytic asymmetric synthesis of γ-hydroxy ketones and aromatic hydroxy ketones by the chemo- and enantio-selective alkylation of keto aldehydes with dialkylzincs

1994; Issue: 21 Linguagem: Inglês

10.1039/p19940003125

2050-8255

Masami Watanabe, Kenso Soai,

Synthetic Organic Chemistry Methods

Optically active γ-hydroxy ketones and aromatic hydroxy ketones with high (up to 96%) enantiomeric excesses have been synthesized by the chemo- and enantio-selective addition of dialkylzincs to γ-keto aldehydes and aromatic keto aldehydes, respectively, using N,N-dibutylnorephedrine (DBNE)1 and (1-methylpyrrolidin-2-yl)diphenylmethanol (DPMPM)5 as chiral catalysts. The method provides a non-homoaldol approach to optically active γ-hydroxy ketones.