A Au(I)-catalyzed protocol for the cycloisomerizations of enynols into 4.3.0 (hetero)bicycles with complete regio- and diastereoselection is herein described. The sequential bicyclization exploits substrates with a styryl arm, disclosing in turn a reactive pathway that is complementary to the literature reports. The use of a gold(I)–phosphite catalyst allowed for the synthesis of functionalized polycycles under mild conditions, with good yields and low catalyst loadings (1 mol%).
Diastereoselective bicyclization of enynols via gold catalysis / Cecchini, Chiara; Cera, Gianpiero; Lanzi, Matteo; Marchiò, Luciano; Malacria, Max; Maestri, Giovanni. - In: ORGANIC CHEMISTRY FRONTIERS. - ISSN 2052-4129. - 6:20(2019), pp. 3584-3588. [10.1039/C9QO00963A]
Diastereoselective bicyclization of enynols via gold catalysis
CECCHINI, CHIARA;Cera, Gianpiero;Lanzi, Matteo;Marchiò, Luciano;Maestri, Giovanni
2019-01-01
Abstract
A Au(I)-catalyzed protocol for the cycloisomerizations of enynols into 4.3.0 (hetero)bicycles with complete regio- and diastereoselection is herein described. The sequential bicyclization exploits substrates with a styryl arm, disclosing in turn a reactive pathway that is complementary to the literature reports. The use of a gold(I)–phosphite catalyst allowed for the synthesis of functionalized polycycles under mild conditions, with good yields and low catalyst loadings (1 mol%).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
