Construction of Optically Active Quaternary Propargyl Amines by Highly Enantioselective Zinc/BINOL-Catalyzed Alkynylation of Ketoimines was written by Huang, Gaochao;Yin, Zengsheng;Zhang, Xingang. And the article was included in Chemistry – A European Journal in 2013.Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol The following contents are mentioned in the article:
A general and efficient method for the highly enantioselective alkynylation of ketoimines through a zinc/1,1′-bi-2-naphthol (BINOL)-catalyzed process has been developed. A variety of ketoimines, including α-fluoroalkyl α-imine esters, α-aryl α-imine esters, and trifluoromethyl aryl ketoimines, are applicable and provide their corresponding quaternary propargyl amines in excellent yields with high ee values (up to 99 % ee). Both the steric and electronic effects of substituents at the 3,3′ positions of BINOL are critical for the reaction efficiency and enantioselectivity. To demonstrate the usefulness of the method, (R)-α-CF3 α-proline has been prepared in a highly efficient manner. The notable features of this protocol are its broad substrate scope, high reaction efficiency (up to 99 %) and enantioselectivity (up to 99 % ee), low catalyst loading (5 mol % of BINOL derivative), and mild reaction conditions. This study involved multiple reactions and reactants, such as (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol).
(R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts