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(14): 2169-2172
DOI: 10.1055/s-2003-41044
DOI: 10.1055/s-2003-41044
PAPER
© Georg Thieme Verlag Stuttgart · New York
Rh(I)-Catalyzed Asymmetric Intramolecular Pauson-Khand Reaction in Aqueous Media
Further Information
Received
20 May 2003
Publication Date:
28 August 2003 (online)
Publication History
Publication Date:
28 August 2003 (online)

Abstract
The first rhodium-BINAP complex-catalyzed enantioselective Pauson-Khand reaction in aqueous media, which is accelerated by surfactant, is reported. The chiral rhodium catalyst is easily prepared in situ from 1 equivalent of [Rh(cod)Cl]2 and 2 equivalents of BINAP under 1 atm of CO and a temperature of 60 °C or 90 °C. Ee’s up to 96% were achieved for the intramolecular Pauson-Khand reaction, but the yields are highly dependent upon the substrate itself.
Key word
Pauson-Khand reaction - rhodium - BINAP - surfactant - aqueous
-
1a
Lindström UM. Chem. Rev. 2002, 102: 2751 -
1b
Aqueous-Phase Organometallic Catalysis
Cornils B.Herrmann WA. Wiley-VCH; Weinheim: 1998. - For recent reviews see:
-
2a
Brummond KM.Kent JL. Tetrahedron 2000, 56: 3263 -
2b
Fletcher AJ.Christie DR. J. Chem. Soc., Perkin Trans. 1 2000, 1657 -
2c
Chung YK. Coord. Chem. Rev. 1999, 188: 297 - 3 Very recently an aqueous-phase stoichiometric Pauson-Khand reaction was reported, see: Kraft M. E., Wright J. A., Boaga L. V. R.; Tetrahedron Lett.; 2003, 44: 3417
-
4a
Sugihara T.Yamaguchi M.Nishizawa M. Chem.-Eur. J. 2001, 7: 1589 -
4b
Sugihara T.Yamaguchi M. Synlett 1998, 1384 - 5
Son SU.Lee SI.Chung YK.Kim S.-W.Hyeon T. Org. Lett. 2002, 4: 277 - For Rh see:
-
6a
Jeong N.Sung BK.Choi YK. J. Am. Chem. Soc. 2000, 122: 6771 -
6b For Ir see:
Shibata T.Takagi K. J. Am. Chem. Soc. 2000, 122: 9852 -
6c For Ti see:
Hick FA.Buchwald SL. J. Am. Chem. Soc. 1996, 118: 11688 -
6d For Co see:
Sturla SJ.Buchwald SL. J. Org. Chem. 2002, 67: 3398 -
6e
Hiroi K.Watanabe T.Kawagishi R.Abe I. Tetrahedron Lett. 2000, 41: 891 - 7 The same crystal structure was reported by Poe et al., see:
Bunten KA.Farrar DH.Poe AJ.Lough A. Organometallics 2002, 21: 3344 - 8
Alami M.Ferri F.Linstrumelle G. Tetrahedron Lett. 1993, 40: 6403