Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2003(12): 1809-1814
DOI: 10.1055/s-2003-41036
DOI: 10.1055/s-2003-41036
PAPER
© Georg ThiemeVerlag Stuttgart · New York
Binaphthyldiamine-Based Diazaphospholidinesas a New Class of Chiral Monodentate P-Ligands
Further Information
Received
2 July 2003
Publication Date:
13 August 2003 (online)
Publication History
Publication Date:
13 August 2003 (online)
Abstract
A new family of chiral diazaphospholidines is readily accessibleby phosphorylating commercially available (S)-1,1′-binaphthyl-2,2′-diamine.NMR spectroscopy, mass spectrometry and X-ray crystallographic analysisreveal their unique structures. In preliminary studies these novelmonodentate P-ligands were tested in Rh-catalyzed hydrogenationand hydroformylation (31% ee) reactions. The modular natureof the ligands allows for further structural diversity.
Key words
asymmetric catalysis - rhodium - phosphorus - hydrogenation - hydroformylation
- 1
Reetz MT.Mehler G. Angew. Chem. Int. Ed. 2000, 39: 3889 ; Angew. Chem. 2000, 112, 4047 - 2
Reetz MT.Sell T. Tetrahedron Lett. 2000, 41: 6333 - 3
Claver C.Fernandez E.Gillon A.Heslop K.Hyett DJ.Martorell A.Orpen AG.Pringle PG. Chem. Commun. 2000, 961 -
4a
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 -
4b
Minnaard AJ.van den Berg M.Schudde EP.van Esch J.deVries AHM.de Vries JG.Feringa BL. Chim.Oggi 2001, 19: 12 - 5
Komarov IV.Börner A. Angew. Chem. Int. Ed. 2001, 40: 1197 ; Angew. Chem. 2001, 113, 1237 -
6a
Reetz MT.Sell T.Meiswinkel A.Mehler G. Angew.Chem. Int. Ed. 2003, 42: 790 ; Angew. Chem. 2003, 115, 814 -
6b
Reetz MT.Mehler G. TetrahedronLett. 2003, 44: 4593 -
6c See also:
Peña D.Minnaard AJ.Boogers JAF.de Vries AHM.de Vries JG.Feringa BL. Org. Biomol. Chem. 2003, 1: 1087 -
7a
Reetz MT.Haderlein G.Angermund K. J. Am. Chem. Soc. 2000, 122: 996 -
7b Chelating bidentate P-ligandsbased on 1:
Miyano S.Nawa M.Mori A.Hashimoto H. Bull. Chem. Soc. Jpn. 1984, 57: 2171 -
7c
Guo R.Li X.Wu J.Kwok WH.Chen J.Choi MCK.Chan ASC. Tetrahedron Lett. 2002, 43: 6803 -
7d
Zhang F.-Y.Kwok WH.Chan ASC. Tetrahedron: Asymmetry 2001, 12: 2337 -
7e
Zhang F.-Y.Pai C.-C.Chan ASC. J.Am. Chem. Soc. 1998, 120: 5808 -
7f See also:
Ansell J.Wills M. Chem. Soc.Rev. 2002, 31: 259 -
8a
Benson SC.Cai P.Colon M.Haiza MA.Tokles M.Snyder JK. J.Org. Chem. 1988, 53: 5335 -
8b
Vyskočil S.Jaracz S.Smrčina M.Štícha M.Hanuš V.Polášek M.Kočovský P. J. Org. Chem. 1998, 63: 7727 - 9
Naberfeld G. Dissertation Ruhr-UniversitätBochum; Germany: 2000. -
10a
Wolfe JP.Wagaw S.Buchwald SL. J. Am. Chem. Soc. 1996, 118: 7215 -
10b
Driver MS.Hartwig JF. J.Am. Chem. Soc. 1996, 118: 7217 - See for example:
-
12a
Brisset H.Gourdel Y.Pellon P.Le Corre M. Tetrahedron Lett. 1993, 34: 4523 -
12b
Imamoto T.Kusumoto T.Suzuki N.Sato K. J. Am. Chem. Soc. 1985, 107: 5301 -
13a
Horiuchi T.Shirakawa E.Nozaki K.Takaya H. Organometallics 1997, 16: 2981 -
13b
Nozaki K.Sakai N.Nanno T.Higashijima T.Mano S.Horiuchi T.Takaya H. J. Am. Chem.Soc. 1997, 119: 4413
References
See experimental section.