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Rhodium‐Catalyzed Intramolecular Hydroacylation of 5‐ and 6‐Alkynals: Convenient Synthesis of α‐Alkylidenecycloalkanones and Cycloalkenones
Author(s) -
Takeishi Kenzo,
Sugishima Koudai,
Sasaki Kaori,
Tanaka Ken
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400679
Subject(s) - hydroacylation , rhodium , intramolecular force , catalysis , chemistry , organic chemistry
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 was unsuccessful. This method represents an attractive new route to highly functionalized α‐alkylidenecycloalkanones and cycloalkenones.