Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis.

Autor: Kavanagh SE; Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland., Gilheany DG; Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2020 Nov 06; Vol. 22 (21), pp. 8198-8203. Date of Electronic Publication: 2020 Oct 19.
DOI: 10.1021/acs.orglett.0c02629
Abstrakt: A series of N -substituted cyclohexyldiaminophenolic ligands for the asymmetric Grignard synthesis of tertiary alcohols is reported. The 2,5-dimethylpyrrole-decorated ligand led to improved enantioselectivities and broadened the scope of the methodology. As an exemplar, we report an unprecedented highly selective one-step synthesis of gossonorol in 93% ee , also constituting the shortest formal syntheses of natural products boivinianin B and yingzhaosu C.
Databáze: MEDLINE