Ring-Opening Cyclization of Spirocyclopropanes Using Sulfoxonium Ylides.
Chem Pharm Bull (Tokyo)
; 68(5): 479-486, 2020.
Article
en En
| MEDLINE
| ID: mdl-32378546
ABSTRACT
Ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes using dimethylsulfoxonium methylide proceeded regioselectively to produce 2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-ones in good to high yields. The reactions of cycloheptane- and cyclopentane-1,3-dione-2-spirocyclopropanes could construct [7.6]- and [5.6]-fused ring systems. This reaction was also carried out using sulfoxonium ethylide, butylide, and benzylide, resulting in the formation of the corresponding 2,3-trans-disubstituted products in good to high yields, and it was shown that the dimethyl group can act as a dummy substituent. It was found that the 2- and 3-phenyhexahydrobenzopyran-5-ones can be readily converted into 5-hydroxyflavan and 5-hydroxyisoflavan, respectively.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Compuestos de Espiro
/
Compuestos de Sulfonio
/
Ciclopropanos
Idioma:
En
Revista:
Chem Pharm Bull (Tokyo)
Año:
2020
Tipo del documento:
Article