Display options
Cite
González-Rodríguez C, Escalante L, Varela JA, et al. Brønsted Acid-promoted intramolecular carbocyclization of alkynals leading to cyclic enones. Org Lett. 2009;11(7):1531-3doi: 10.1021/ol900142r.
González-Rodríguez, C., Escalante, L., Varela, J. A., Castedo, L., & Saá, C. (2009). Brønsted Acid-promoted intramolecular carbocyclization of alkynals leading to cyclic enones. Organic letters, 11(7), 1531-3. https://doi.org/10.1021/ol900142r
González-Rodríguez, Carlos, et al. "Brønsted Acid-promoted intramolecular carbocyclization of alkynals leading to cyclic enones." Organic letters vol. 11,7 (2009): 1531-3. doi: https://doi.org/10.1021/ol900142r
González-Rodríguez C, Escalante L, Varela JA, Castedo L, Saá C. Brønsted Acid-promoted intramolecular carbocyclization of alkynals leading to cyclic enones. Org Lett. 2009 Apr 02;11(7):1531-3. doi: 10.1021/ol900142r. PMID: 19245263.
Copy Download .nbib Format: NLM
Share it on

Org Lett. 2009 Apr 02;11(7):1531-3. doi: 10.1021/ol900142r.

Brønsted Acid-promoted intramolecular carbocyclization of alkynals leading to cyclic enones.

Organic letters

Carlos González-Rodríguez, Luz Escalante, Jesús A Varela, Luis Castedo, Carlos Saá

Affiliations

  1. Departamento de Quimica Organica, Facultad de Quimica, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.

PMID: 19245263 DOI: 10.1021/ol900142r

Abstract

TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.

Publication Types