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A GaCl 3 -Catalyzed [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds and Isocyanides Leading to Unsaturated γ-Lactone Derivatives

2003; American Chemical Society; Volume: 125; Issue: 26 Linguagem: Inglês

10.1021/ja035014u

1943-2984

Naoto Chatani, Masayuki Oshita, Mamoru Tobisu, Yutaka Ishii, Shinji Murai,

Chemical Synthesis and Analysis

A GaCl3-catalyzed reaction of alpha,beta-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 alpha,beta-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.