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A GaCl3-Catalyzed [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds and Isocyanides Leading to Unsaturated γ-Lactone Derivatives

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journal contribution
posted on 10.06.2003 by Naoto Chatani, Masayuki Oshita, Mamoru Tobisu, Yutaka Ishii, Shinji Murai
A GaCl3-catalyzed reaction of α,β-unsaturated ketones with isocyanides leading to the formation of unsaturated lactone derivatives is described. This is the first example of the catalytic [4+1] cycloaddition of α,β-unsaturated ketones and isocyanides. GaCl3 is an excellent catalyst due to its lower oxophilicity, which is desirable for all of the key steps, such as E/Z isomerization, cyclization, and deattachment from the products.