ISSN:
0570-0833
Keywords:
Cycloaddition
;
Synthetic methods
;
Cobalt catalysts
;
Catalysis
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Dicarbonyl (η5-cyclopentadienyl)cobalt functions as a matrix on which a variety of unsaturated organic substrates undergo mutual bond formation. In this way α,ω-diynes cocyclize with monoalkynes to give annelated benzenes, while o-diethynylbenzenes furnish biphenylenes, and α,ω-enynes lead to the formation of complexed bi-and tricyclic dienes. Nitriles cocyclize with two alkynyl groups to give pyridines and other heterocycles, isocyanates allow access to annelated 2-pyridones, and incorporation of carbon monoxide provides complexed cyclopentadienones. In many cases remarkable chemo-, regio-, and stereoselectivity are observed, partially facilitated by use of the trimethylsilyl substituent as a controlling group. The scope and level of maturity of the method are demonstrated by the synthesis of a series of hitherto inaccessible, novel, and theoretically interesting molecules, and by its utilization in several unique approaches to a variety of natural products, e.g. protoberberines, steroids, vitamin B6, and camptothecin.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.198405393
