Catalytic asymmetric synthesis of γ-hydroxy ketones and aromatic hydroxy ketones by the chemo- and enantio-selective alkylation of keto aldehydes with dialkylzincs
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 21,p. 3125-3128
- https://doi.org/10.1039/p19940003125
Abstract
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.Keywords
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