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Enantiocontrolled Synthesis of Tertiary α‐Hydroxy‐α‐ynyl Esters by Dimethylzinc‐Mediated Addition of Alkynes to α‐Keto Esters
Author(s) -
Infante Rebeca,
Gago Alfonso,
Nieto Javier,
Andrés Celia
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200185
Subject(s) - chemistry , dimethylzinc , lewis acids and bases , nucleophilic addition , homogeneous , organic chemistry , nucleophile , catalysis , physics , thermodynamics
A perhydro‐1,3‐benzoxazine behaves as an excellent chiral ligand in the nucleophilic addition of alkynylzinc derivatives, prepared from terminal alkynes and dimethylzinc, to α‐keto esters without using other Lewis acids. The enantioselectivity is excellent and homogeneous for a wide variety of aromatic and heteroaromatic α‐keto esters. Aliphatic enolizable α‐keto esters were alkynylated with moderate enantioselection.