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(19): 3183-3185
DOI: 10.1055/s-2005-918460
DOI: 10.1055/s-2005-918460
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Rhodium-Catalyzed Enantioselective Hydrogenation of β,β-Disubstituted α-Acetamido Acrylates Using Cheap Monodentate P-Ligands
Weitere Informationen
Received
28 September 2005
Publikationsdatum:
14. November 2005 (online)
Publikationsverlauf
Publikationsdatum:
14. November 2005 (online)

Abstract
The asymmetric Rh-catalyzed hydrogenation of β,β-disubstituted α-acetamido acrylates, which are notoriously difficult substrates, is possible using readily available BINOL-derived monodentate phosphites or phosphonites. Essentially quantitative conversion and enantioselectivities of 95-97% ee are readily achieved, making the process industrially viable.
Key words
amino acids - asymmetric catalysis - hydrogenations - rhodium - chiral auxiliaries
-
1a
Knowles WS. Angew. Chem. Int. Ed. 2002, 41: 1998 ; Angew. Chem. 2002, 114, 2096 -
1b
Noyori R. Angew. Chem. Int. Ed. 2002, 41: 2008 ; Angew. Chem. 2002, 114, 2108 - 2
Blaser HU.Spindler F.Studer M. Appl. Catal. A: Gen. 2001, 221: 119 -
3a
Reetz MT.Mehler G. Angew. Chem. Int. Ed. 2000, 39: 3889 ; Angew. Chem. 2000, 112, 4047 -
3b
Reetz MT.Mehler G.Meiswinkel A.Sell T. Tetrahedron Lett. 2002, 43: 7941 -
3c
Reetz MT.Goossen LJ.Meiswinkel A.Paetzold J.Feldthusen Jensen J. Org. Lett. 2003, 5: 3099 -
3d
Reetz MT. In Perspectives in Organometallic ChemistryScrettas CG.Steele BR. Royal Society of Chemistry; Cambridge: 2003. p.265-274 -
3e
Reetz MT.Bondarev OG.Gais H.-J.Bolm C. Tetrahedron Lett. 2005, 46: 5643 -
3f
Reetz MT,Mehler G, andMeiswinkel A. inventors; Pat. Appl., DE-A 10027505.2. ; Chem. Abstr. 2002, 136, 20159 - 4
Reetz MT.Sell T. Tetrahedron Lett. 2000, 41: 6333 - 5
Claver C.Fernandez E.Gillon A.Heslop K.Hyett DJ.Martorell A.Orpen AG.Pringle PG. Chem. Commun. 2000, 961 -
6a
van den Berg M.Minnaard AJ.Schudde EP.van Esch J.de Vries AHM.de Vries JG.Feringa BL. J. Am. Chem. Soc. 2000, 122: 11539 -
6b
Minnaard AJ.van den Berg M.Schudde EP.van Esch J.de Vries AHM.de Vries JG.Feringa BL. Chim. Oggi 2001, 19: 12 -
6c
Bernsmann H.van den Berg M.Hoen R.Minnaard AJ.Mehler G.Reetz MT.de Vries JG.Feringa BL. J. Org. Chem. 2005, 70: 943 -
6d
Reetz MT.Ma J.-A.Goddard R. Angew. Chem. Int. Ed. 2005, 44: 412 ; Angew. Chem. 2005, 117, 416 - 7
Reetz MT.Meiswinkel A.Mehler G.Angermund K.Graf M.Thiel W.Mynott R.Blackmond DG. J. Am. Chem. Soc. 2005, 127: 10305 - Further examples and other types of monodentate P-ligands:
-
8a
Junge K.Hagemann B.Enthaler S.Oehme G.Michalik M.Monsees A.Riermeier T.Dingerdissen U.Beller M. Angew. Chem. Int. Ed. 2004, 43: 5066 ; Angew. Chem. 2004, 116, 5176 -
8b
Komarov IV.Börner A. Angew. Chem. Int. Ed. 2001, 40: 1197 ; Angew. Chem. 2001, 113, 1237 -
8c
Ostermeier M.Prieß J.Helmchen G. Angew. Chem. Int. Ed. 2002, 41: 612 ; Angew. Chem. 2002, 114, 625 -
8d
Chi Y.Zhang X. Tetrahedron Lett. 2002, 43: 4849 -
8e
Chen W.Xiao J. Tetrahedron Lett. 2001, 42: 8737 -
8f
Huang H.Zheng Z.Luo H.Bai C.Hu X.Chen H. J. Org. Chem. 2004, 69: 2355 -
8g
Hu A.-G.Fu Y.Xie J.-H.Zhou H.Wang L.-X.Zhou Q.-L. Angew. Chem. Int. Ed. 2002, 41: 2348 ; Angew. Chem. 2002, 114, 2454 -
8h
Pakulski Z.Demchuk OM.Frelek J.Luboradzki R.Pietrusiewicz KM. Eur. J. Org. Chem. 2004, 3913 -
8i
Jerphagnon T.Renaud J.-L.Bruneau C. Tetrahedron: Asymmetry 2004, 15: 2101 -
8j
Lagasse F.Kagan HB. Chem. Pharm. Bull. 2000, 48: 315 -
8k
Ansell J.Wills M. Chem. Soc. Rev. 2002, 31: 259 -
9a
Reetz MT.Sell T.Meiswinkel A.Mehler G. Angew. Chem. Int. Ed. 2003, 42: 790 ; Angew. Chem. 2003, 115, 814 -
9b
Reetz MT.Li X. Tetrahedron 2004, 60: 9709 -
9c
Reetz MT.Mehler G.Meiswinkel A.Sell T. Tetrahedron: Asymmetry 2004, 15: 2165 -
9d
Reetz MT.Li X. Angew. Chem. Int. Ed. 2005, 44: 2959 ; Angew. Chem. 2005, 117, 3019 -
9e
Reetz MT,Sell T,Meiswinkel A, andMehler G. inventors; Pat. Appl., DE-A 10247633.0. ; Chem. Abstr. 2004, 140, 381359 -
9f See also:
Peña D.Minnaard AJ.Boogers JAF.de Vries AHM.de Vries JG.Feringa BL. Org. Biomol. Chem. 2003, 1: 1087 -
10a
Burk MJ.Gross MF.Martinez JP. J. Am. Chem. Soc. 1995, 117: 9375 -
10b
Sawamura M.Kuwano R.Ito Y. J. Am. Chem. Soc. 1995, 117: 9602 -
10c
Imamoto T.Watanabe J.Wada Y.Masuda H.Yamada H.Tsuruta H.Matsukawa S.Yamaguchi K. J. Am. Chem. Soc. 1998, 120: 1635 -
10d
Ohashi A.Kikuchi S.-I.Yasutake M.Imamoto T. Eur. J. Org. Chem. 2002, 2535 -
10e
Evans DA.Michael FE.Tedrow JS.Campos KR. J. Am. Chem. Soc. 2003, 125: 3534 -
10f
Hoge G.Wu H.-P.Kissel WS.Pflum DA.Greene DJ.Bao J. J. Am. Chem. Soc. 2004, 126: 5966