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

Autor:	Declan G. Gilheany, Saranna E Kavanagh
Rok vydání:	2020
Předmět:	Scope (project management) 010405 organic chemistry Chemistry Ligand Organic Chemistry Gossonorol One-Step 010402 general chemistry Highly selective 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Physical and Theoretical Chemistry Tertiary alcohols
Zdroj:	Organic Letters. 22:8198-8203
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.0c02629
Popis:	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:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8af168c0e7e4c9c59f726027796656e1 https://doi.org/10.1021/acs.orglett.0c02629 Zobrazit plný text záznamu