Rhodium??Catalyzed Intramolecular Hydroacylation of 5??and 6??Alkynals: Convenient Synthesis of α??Alkylidenecycloalkanones and Cycloalkenones

K Takeishi, K Sugishima, K Sasaki…

Index: Takeishi, Kenzo; Sugishima, Koudai; Sasaki, Kaori; Tanaka, Ken Chemistry - A European Journal, 2004 , vol. 10, # 22 p. 5681 - 5688

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Citation Number: 68

Abstract

Abstract A novel intramolecular hydroacylation of 5-and 6-alkynals leading to α- alkylidenecycloalkanones was accomplished by using cationic a rhodium (I)/BINAP complex. For all cyclizations described, a single (E)-olefin isomer was obtained. At elevated temperature, hydroacylation and double bond migration of 5-and 6-alkynals proceeded in a one-pot reaction to give cycloalkenones. An intramolecular hydroacylation of a 7-alkynal ...