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Highly Regio‐ and Stereoselective Synthesis of Nine‐ to Twelve‐Membered Cyclic Compounds by a Pd 0 ‐Catalyzed Cyclization Reaction between Allenes with a Nucleophilic Functionality and Organic Halides
Author(s) -
Jiang Xinpeng,
Yang Qing,
Yu Yihua,
Fu Chunling,
Ma Shengming
Publication year - 2009
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.200900972
Subject(s) - chemistry , allene , nucleophile , stereoselectivity , moiety , medicinal chemistry , intramolecular force , catalysis , intramolecular reaction , palladium , nucleophilic addition , chlorosilane , stereochemistry , organic chemistry , silicon
Simple cyclization : A novel method has been developed for the highly regio‐ and stereoselective synthesis of nine‐ to twelve‐membered cyclic compounds by a Pd 0 ‐catalyzed cyclization reaction of allenes with a carbon or nitrogen nucleophilic functionality. Oxidative addition and carbopalladation gave anti ‐π‐allyl palladium intermediates, then an exclusive intramolecular nucleophilic attack at the terminal carbon atom of the allene moiety gave the E product in good yields (see scheme; Ts=tosyl; DMA= N , N ‐dimethylacetamide).