Regioselective Hydrostannation of Allenes Catalyzed by Pd(OH)2/C
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Publisher
Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference12 articles.
1. a) Stille, J.K. Pure & Appl. Chem. 1985, 57, 1771. b) Pereyre, M.; Quintard, J.P.; Rahm, A. Tin in Organic Synthesis Butterworths: London, 1987.
2. a) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1329. b) Lautens, M.; Klute, W. Angew. Chem. Int. Ed. Engl. 1996, 35, 442. (c) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10668.
3. Hydrostannation and Hydrogermylation of Allenes
4. a) Mitchell, T.N.; Schneider, U. J. Organomet. Chem. 1991, 405, 195. b) Koerber, K.; Gore, J.; Vatele, J.M. Tetrahedron Lett. 1991, 32, 1187. c) Ichinose, Y.; Oshima, K. Utimoto, K. Bull. Chem. Soc. Jpn. 1988, 61, 2693. d) Palladium (0) also catalyzes the addition of carbon “pronucleophiles” to allenes to give products equivalent to allylic substitution, see: Trost, B.M.; Gerusz, V.J. J. Am. Chem. Soc. 1995, 117, 5156. e) Palladium catalyzed addition to the central carbon of an allene followed by cyclization is known, see: Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A. J. Org. Chem. 1991, 56, 2615. In this study the mechanism is proposed to occur via carbopalladation to form a π-allyl intermediate which is analogous to intermediates 23 and 25 in Scheme. 4. f) Following the submission of our manuscript, Yamamoto reported palladium and Lewis acid catalysts are useful for the preparation of allyl and vinylstannanes, see: Gevorgyan, V.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2963.
5. Studies in the Directed Cyclopropanation of .alpha.-Allenic Alcohols
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