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

Neyyappadath, Rifahath M; Cordes, David B; Slawin, Alexandra M Z; Smith, Andrew D

Neyyappadath, Rifahath M; Cordes, David B; Slawin, Alexandra M Z; Smith, Andrew D.

Afiliación

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.

Chem Commun (Camb) ; 53(17): 2555-2558, 2017 Feb 23.

Article en En | MEDLINE | ID: mdl-28133660

ABSTRACT

ABSTRACT

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.

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Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2017 Tipo del documento: Article País de afiliación: Reino Unido

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