4.5 Article

Estrone derived 2-naphthol analogue in the diastereoselective one-pot Betti-condensation

期刊

MOLECULAR DIVERSITY
卷 24, 期 4, 页码 1343-1353

出版社

SPRINGER
DOI: 10.1007/s11030-019-09998-5

关键词

Deoxy-isoequilenine; Betti-condensation; Chiral ligands; Absolute configuration; Diethylzinc addition

资金

  1. National Science Fund, Bulgaria [UNA 17/2005, DRNF 02/13/2009, DRNF-02/1/2009]

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The utility of deoxy-isoequilenine synthesized from estrone as valuable 2-naphthol analogue is demonstrated in the three components Betti-condensation. A simple, efficient and green procedure for the synthesis of aminobenzylnaphthol analogues (so-called Betti bases) has been realized highly diastereoselectively by using (S)-phenylethylamine and 1- or 2-naphthaldehyde. The absolute configuration of the new chiral compounds obtained has been determined by means of NMR experiments and confirmed by X-ray crystallography. The chiral steroidal aminobenzylnaphthols have been evaluated as pre-catalysts for the addition of diethylzinc to aldehydes with enantioselectivities of up to 98% ee.

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