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Synthesis 2009(13): 2289-2292
DOI: 10.1055/s-0029-1216848
DOI: 10.1055/s-0029-1216848
PSP
© Georg Thieme Verlag
Stuttgart ˙ New YorkBinaphthyl-Modified Quaternary Phosphonium Salts as Chiral Phase Transfer Catalysts: Application to Asymmetric Amination of β-Keto Esters
Weitere Informationen
Received
13 March 2009
Publikationsdatum:
29. Mai 2009 (online)
Publikationsverlauf
Publikationsdatum:
29. Mai 2009 (online)

Abstract
A chiral quaternary tetraalkylphosphonium salt has been successfully utilized for the first time as a phase-transfer catalyst for asymmetric amination of β-keto esters in high yield with high ee. Asymmetric amination of a cyclic five-membered β-keto ester is a valuable method for preparing a key intermediate for asymmetric synthesis of aldose reductase inhibitor AS-3201 (Ranirestat).
Key words
amination - asymmetric synthesis - phase-transfer catalysis - phosphonium salts
- 1a
Dehmlow EV.Dehmlow SS. Phase Transfer Catalysis 3rd ed.: VCH; Weinheim: 1993. - 1b
Starks CM.Liotta CL.Halpern M. Phase-Transfer Catalysis Chapman & Hall; New York: 1994. - 1c
Handbook
of Phase-Transfer Catalysis
Sasson Y.Neumann R. Blackie Academic & Professional; London: 1997. - 1d
Phase-Transfer
Catalysis
Halpern ME. ACS Symposium Series 659, American Chemical Society; Washington DC: 1997. - For representative reviews on asymmetric phase-transfer catalysis, see:
- 2a
O’Donnell MJ. In Catalytic Asymmetric SynthesisOjima I. VCH; Weinheim: 1993. Chap. 8. - 2b
Shioiri T. In Handbook of Phase-Transfer CatalysisSasson Y.Neumann R. Blackie Academic & Professional; London: 1997. Chap. 14. - 2c
O’Donnell MJ. Phases-The Sachem Phase Transfer Catalysis Review 1998, Issue 4: 5 - 2d
O’Donnell MJ. Phases-The Sachem Phase Transfer Catalysis Review 1999, Issue 5: 5 - 2e
Nelson A. Angew. Chem. Int. Ed. 1999, 38: 1583 - 2f
Shioiri T.Arai S. In Stimulating Concepts in ChemistryVogtle F.Stoddart JF.Shibasaki M. Wiley-VCH; Weinheim: 2000. p.123 - 2g
O’Donnell MJ. In Catalytic Asymmetric Synthesis 2nd ed.:Ojima I. Wiley-VCH; New York: 2000. Chap. 10. - 2h
O’Donnell MJ. Aldrichimica Acta 2001, 34: 3 - 2i
Maruoka K.Ooi T. Chem. Rev. 2003, 103: 3013 - 2j
O’Donnell MJ. Acc. Chem. Res. 2004, 37: 506 - 2k
Lygo B.Andrews BI. Acc. Chem. Res. 2004, 37: 518 - 2l
Vachon J.Lacour J. Chimia 2006, 60: 266 - 2m
Ooi T.Maruoka K. Angew. Chem. Int. Ed. 2007, 46: 4222 - 2n
Hashimoto T.Maruoka K. Chem. Rev. 2007, 107: 5656 - 2o
Ooi T.Maruoka K. Aldrichimica Acta 2007, 40: 77 - 2p
Maruoka K. Org. Process Res. Dev. 2008, 12: 679 - 3a
Yonemori S.Hayashi Y.Kumai S.Wada A. Nippon Kagaku Kaishi 1991, 8: 1146 - 3b
Phase-Transfer Catalysis:
Fundamentals, Applications, and Industrial Perspectives
Starks CM.Liotta CL.Halpern M. Chapman & Hall; New York: 1994. p.132 - 4a
Manabe K. Tetrahedron Lett. 1998, 39: 5807 - 4b
Manabe K. Tetrahedron 1998, 54: 14465 - 4c
Kohler M. Dissertation RWTH Aachen University; Germany: 2003. - For selected examples of asymmetric amination of β-keto esters, see:
- 5a
Juhl K.Jørgensen KA. J. Am. Chem. Soc. 2002, 124: 2420 - 5b
Marigo M.Juhl K.Jørgensen KA. Angew. Chem. Int. Ed. 2003, 42: 1367 - 5c
Saaby S.Bella M.Jørgensen KA. J. Am. Chem. Soc. 2004, 126: 8120 - 5d
Ma S.Jiao N.Zheng Z.Ma Z.Lu Z.Ye L.Deng Y.Chen G. Org. Lett. 2004, 6: 2193 - 5e
Pihko PM.Pohjakallio A. Synlett 2004, 2115 - 5f
Liu X.Li H.Deng L. Org. Lett. 2005, 7: 167 - 5g
Foltz C.Stecker B.Marconi G.Bellemin-Laponnaz S.Wadepohl H.Gabe LH. Chem. Commun. 2005, 5115 - 5h
Xu X.Yabuta T.Yuan P.Takemoto Y. Synlett 2006, 137 - 5i
Kang YK.Kim DY. Tetrahedron Lett. 2006, 47: 4565 - 5j
Terada M.Nakano M.Ube H. J. Am. Chem. Soc. 2006, 128: 16044 - 5k
Comelles J.Pericas A.Moreno-Manas M.Vallribera A.Drudis-Sole G.Lledos A.Parella T.Roglans A.Garcia-Granda S.Roces-Fernandez L. J. Org. Chem. 2007, 72: 2077 - 5l
He R.Wang X.Hashimoto T.Maruoka K. Angew. Chem. Int. Ed. 2008, 47: 9466 - For representative reviews on asymmetric α-amination reactions, see:
- 6a
Genet J.-P.Creck C.Lavergne D. In Modern Amination MethodsRicci A. Wiley-VCH; Weinheim: 2000. Chap. 3. - 6b
Greck C.Drouillat B.Thomassigng C. Eur. J. Org. Chem. 2004, 1377 - 6c
Erdik E. Tetrahedron 2004, 60: 8742 - 6d
Janey JM. Angew. Chem. Int. Ed. 2005, 44: 4292 - 6e
Najera C.Sansano JM. Chem. Rev. 2007, 107: 4584 - 7a
Negoro T.Murata M.Ueda S.Fujitani B.Ono Y.Kuromiya A.Suzuki K.Matsumoto J.-I. J. Med. Chem. 1998, 41: 4118 - 7b
Kurono M.Fujiwara I.Yoshida K. Biochemistry 2001, 40: 8216 - 7c
Bril V.Buchanan RA. Diabetes Care 2004, 27: 2369 - 7d
Kurono M.Fujii A.Murata M.Fujitani B.Negoro T. Biochem. Pharmacol. 2006, 71: 338 - 7e
Giannoukakis N. Curr. Opin. Invest. Drugs 2006, 7: 916 - 7f
Mashiko T.Hara K.Tanaka D.Fujiwara Y.Kumagai N.Shibasaki M. J. Am. Chem. Soc. 2007, 129: 11342 - 7g
Mashiko T.Kumagai N.Shibasaki M. Org. Lett. 2008, 10: 2725 - 8
Ooi T.Kameda M.Maruoka K. J. Am. Chem. Soc. 2003, 125: 5139 - 9
Busacca CA.Lorenz JC.Grinberg N.Haddad N.Hrapchak M.Latli B.Lee H.Sabila P.Saha A.Sarvestani M.Shen S.Varsolona R.Wei X.Senanayake CH. Org. Lett. 2005, 7: 4277