6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis.

Autor: Neyyappadath RM; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk., Cordes DB; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk., Slawin AM; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk., Smith AD; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2017 Feb 23; Vol. 53 (17), pp. 2555-2558.
DOI: 10.1039/c6cc10178j
Abstrakt: The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.
Databáze: MEDLINE