RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2009(14): 2385-2392
DOI: 10.1055/s-0029-1217395
DOI: 10.1055/s-0029-1217395
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkNovel Synthesis of Medium-Sized Heterocycles by Palladium-Catalyzed Intramolecular Heck Reaction via 9-endo-trig Mode of Cyclization
Weitere Informationen
Received
8 February 2009
Publikationsdatum:
08. Juni 2009 (online)
Publikationsverlauf
Publikationsdatum:
08. Juni 2009 (online)

Abstract
An efficient and high yielding method for the synthesis of nine-membered heterocyclic skeletons has been developed by palladium-catalyzed intramolecular Heck reaction via an unusual 9-endo-trig mode of cyclization.
Key words
intramolecular Heck reaction - palladium acetate - 9-endo-trig - nine-membered ring - Claisen rearrangement
- 1a
Horwell DC.Nichols PD.Ratcliffe GS.Roberts E. J. Org. Chem. 1994, 59: 4418 - 1b
Gibson (nee Thomas) SE.Jones JO.McCague R.Tozer MJ.Whitcombe NJ. Synlett 1999, 954 - 1c
Kalinin AV.Chauder BA.Rakhit S.Snieckus V. Org. Lett. 2003, 5: 3519 - 2a
Illuminati G.Mandolini L. Acc. Chem. Res. 1981, 14: 95 - 2b
Mehta G.Singh V. Chem. Rev. 1999, 99: 881 - 2c
Yet L. Chem. Rev. 2000, 100: 2963 - 3
Carl KL. inventors; US Patent 4 073 912. ; Chem. Abstr. 1978, 89, 24156 - 4
D’Amico JJ. inventors; Monsanto Co., British Patent 1 167 084. ; Chem. Abstr. 1970, 72, 12603y - 5
Arnold B,Benjamin P, andSheldon S. inventors; (Hoffmann-La Roche F. and Co. AG) German Patent 2 353 062. ; Chem. Abstr. 1974, 81, 3748n - 6a
Majumdar KC.Chattopadhyay B.Ray K. Tetrahedron Lett. 2007, 48: 7633 - 6b
Majumdar KC.Chattopadhyay B.Sinha B. Tetrahedron Lett. 2008, 49: 1319 - 7a
Linde HHA. Helv. Chim. Acta 1965, 48: 1822 - 7b
Abraham DJ.Rosenstein RD.Lyon RL.Fong HHS. Tetrahedron Lett. 1972, 13: 909 - 8
Kam T.-S.Tee Y.-M.Subramaniam G. Nat. Prod. Lett. 1988, 12: 307 - 9
Baudoin O.Guenard D.Gueritte F. Mini-Rev. Org. Chem. 2004, 1: 333 - 10a
Majumdar KC.Chattopadhyay B.Taher A. Synthesis 2007, 3647 - 10b
Majumdar KC.Pal AK.Taher A.Debnath P. Synthesis 2007, 1701 - 10c
Majumdar KC.Chattopadhyay B. Synlett 2008, 979 - 10d
Majumdar KC.Chattopadhyay B.Nath S. Tetrahedron Lett. 2008, 49: 1609 - 10e
Majumdar KC.Chattopadhyay B.Pal AK. Lett. Org. Chem. 2008, 5: 276 - 11a
Beletskaya IP.Cheprakov AV. Chem. Rev. 2000, 100: 3009 - 11b
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 - 11c
Milne JE.Buchwald SL. J. Am. Chem. Soc. 2004, 126: 13028 - 12a
Christoph G.Buchwald SL. Chem. Eur. J. 1999, 5: 3107 - 12b
Bumagin NA.Bykov VV.Sukhomlinova LI.Tolstaya TP.Beletskaya IP. J. Organomet. Chem. 1995, 486: 259 - 12c
Bumagin NA.More PG.Beletskaya IP. J. Organomet. Chem. 1989, 371: 397 - 13
Arnold LA.Luo W.Guy RK. Org. Lett. 2004, 6: 3005 - 14
Otter BA.Taube A.Fox JJ. J. Org. Chem. 1971, 36: 1251 - 15a
Gazith M.Noys RM. J. Am. Chem. Soc. 1955, 77: 6091 - 15b
Gardner IJ.Noys RM. J. Am. Chem. Soc. 1961, 83: 2409 - 16
Majumdar KC.Khan AT. Synth. Commun. 1987, 17: 1589 - 17
Gibson SE.Guillo N.Middleton RJ.Thuilliez A.Tozer MJ. J. Chem. Soc., Perkin Trans. 1 1997, 447