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Asymmetric cyclization–carbonylation of 2-propargyl-1,3-dione

✍ Scribed by Keisuke Kato; Maki Tanaka; Shigeo Yamamura; Yasuhiro Yamamoto; Hiroyuki Akita

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
291 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first example of asymmetric cyclization-carbonylation of 2-propargyl-1,3-dione 1 catalyzed by palladium(II) with chiral bisoxazolines (C.H.-BOX) was investigated. The use of bulky alcohols increased the ee of the products 2. The product 2d was converted into bicyclic enones 7 and 8, a useful intermediate for the synthesis of natural products.

📜 SIMILAR VOLUMES

Cyclization–Carbonylation–Cyclization Co
Cyclization–Carbonylation–Cyclization Coupling Reactions of Propargyl Acetates and Amides with Palladium(II)–Bisoxazoline Catalysts
✍ Sumie Yasuhara; Makiko Sasa; Dr. Taichi Kusakabe; Dr. Hiroyuki Takayama; Prof. D 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 324 KB 👁 1 views

Scheme 1. Our concept of a cyclization-carbonylation-cyclization coupling reaction (CCC coupling reaction) of propargylic compounds. Scheme 2. Previous studies: ligand-controlled tandem carbonylative cyclization of propargyl acetates. tfa = trifluoroacetate.