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 2005(4): 668-672
DOI: 10.1055/s-2004-831211
DOI: 10.1055/s-2004-831211
PSP
© Georg Thieme Verlag Stuttgart · New York
Chemoselective Deprotection of Allylic Amines Catalyzed by Grubbs’ Carbene
Weitere Informationen
Received
5 May 2004
Publikationsdatum:
21. Oktober 2004 (online)
Publikationsverlauf
Publikationsdatum:
21. Oktober 2004 (online)
Abstract
A commercially available ruthenium complex (first generation Grubbs’ carbene) was used for the catalytic deprotection of allylic amines (secondary as well as tertiary), by using for the first time reagents different from palladium catalysts. Interestingly, the catalytic system directs the reaction toward the selective deprotection of allylamines in the presence of allylic ethers.
Key words
amines - carbenes - catalytic cleavage - protecting groups - ruthenium
-
1a
Greene TW.Wuts GM. In Protective Groups in Organic Synthesis 3rd. ed.: Wiley; New York: 1999. -
1b
Kocienski PJ. Protecting Groups 3rd ed.: Thieme; Stuttgart: 2003. - 2 For an Ir-catalyzed deprotection of allylamides, see:
Neugnot B.Cintrat J.-C.Rousseau B. Tetrahedron 2004, 60: 3575 - 3 For a review, see:
Guibé F. Tetrahedron 1998, 54: 2967 -
4a Review:
Alcaide B.Almendros P. Chem. Eur. J. 2003, 9: 1258 -
4b See also:
Schmidt B. Angew. Chem. Int. Ed. 2003, 42: 4996 -
4c See also:
Schmidt B. Eur. J. Org. Chem. 2004, 1865 -
4d For a recent paper, see:
Hong SH.Day MW.Grubbs RH. J. Am. Chem. Soc. 2004, 126: 7414 - 5
Schwab P.Grubbs RH.Ziller JW. J. Am. Chem. Soc. 1996, 118: 100 -
6a
Alcaide B.Almendros P.Alonso JM.Aly MF. Org. Lett. 2001, 3: 3781 -
6b
Alcaide B.Almendros P.Alonso JM. Chem. Eur. J. 2003, 9: 5793