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Cyclic Metalated Nitriles: Stereoselective Cyclizations to cis ‐ and trans ‐Hydrindanes, Decalins, and Bicyclo[4.3.0]undecanes
Author(s) -
Fleming Fraser F.,
Gudipati Subramanyham
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800715
Subject(s) - chemistry , nitrile , stereoselectivity , bicyclic molecule , nucleophile , stereochemistry , nucleophilic addition , solvent , organic chemistry , catalysis
Metalated nitriles are nucleophilic chameleons whose precise identity is determined by the nature of the metal, the solvent, the temperature, and the structure of the nitrile. The review surveys the different structural types and their cyclization trajectories to show how to selectively tune the metalated nitrile geometry for stereoselective cyclizations to a variety of cis or trans hydrindanes, decalins, and bicyclo[4.3.0]undecanes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)