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 2007(20): 3257-3260
DOI: 10.1055/s-2007-983830
DOI: 10.1055/s-2007-983830
PSP
© Georg Thieme Verlag Stuttgart · New York
A Conjugate Reduction Pathway to Chiral Silanes Using CuH
Weitere Informationen
Received
28 March 2007
Publikationsdatum:
30. Juli 2007 (online)
Publikationsverlauf
Publikationsdatum:
30. Juli 2007 (online)
Abstract
Experimental details concerning asymmetric 1,4-reduction of β-silylated-β,β-disubstituted enoates catalyzed by CuH are described. High yields and enantiomeric excesses are to be expected when Solvias’ JOSIPHOS bis-phosphine PPF-P(t-Bu)2 is used as a nonracemic ligand.
Key words
chiral silanes - CuH - asymmetric conjugate reduction
-
1a
Jones GR.Landais Y. Tetrahedron 1996, 52: 7599 -
1b
Hiyama T.Shirakawa E. In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1:Negishi E. Wiley; Hoboken, NJ: 2002. p.285 -
1c
Chabaud L.James P.Landais Y. Eur. J. Org. Chem. 2004, 3173 -
1d
Fleming I.Barbero A.Walter D. Chem. Rev. 1997, 97: 2063 -
1e
Panek JS.Masse CE. Chem. Rev. 1995, 95: 1293 -
1f
Nishiyama H.Itoh K. Asymmetric Hydrosilylation and Related Reactions, In Catalytic Asymmetric SynthesisOjima I. Wiley-VCH; Weinheim: 2000. Chap. 2. -
1g
Rendler S.Auer G.Oestreich M. Angew. Chem. Int. Ed. 2005, 44: 7620 -
2a
Tamao K.Ishida N.Kumada M. J. Org. Chem. 1983, 48: 2120 -
2b
Tamao K.Ishida N.Tanaka T.Kumada M. Organometallics 1983, 2: 1694 - 3
Fleming I.Henning R.Plaut H. J. Chem. Soc., Chem. Commun. 1984, 29 - 4
Suginome M.Ohmura T.Miyake Y.Mitani S.Ito Y.Murakami M. J. Am. Chem. Soc. 2003, 125: 11174 -
5a
Hayashi T.Matsumoto Y.Ito Y. J. Am. Chem. Soc. 1988, 110: 5579 -
5b
Hayashi T.Shintani R.Okamoto K. Org. Lett. 2005, 7: 4757 -
5c
Oestreich M.Walter C.Auer G. Angew. Chem. Int. Ed. 2006, 45: 5675 - 6
Lipshutz BH.Tanaka N.Taft BR.Lee C.-T. Org. Lett. 2006, 8: 1963 -
7a
Fleming I.Newton TW.Roessler F. J. Chem. Soc., Perkin Trans. 1 1981, 2527 -
7b
Scheidt KA.Clark CT.Milgram BC. Org. Lett. 2004, 6: 3977 - 8
Fujiwara T.Sawabe K.Takeda T. Tetrahedron 1997, 53: 8349 - 9
Lipshutz BH.Noson K.Chrisman W.Lower A. J. Am. Chem. Soc. 2003, 125: 8779 - 11
Stryker JM.Mahoney WS. J. Am. Chem. Soc. 1989, 111: 8818 - 12
Lipshutz BH.Chrisman W.Noson K.Papa P.Sclafani JA.Vivian RW.Keith JM. Tetrahedron 2000, 56: 2779 -
13a
Lipshutz BH.Frieman BA. Angew. Chem. Int. Ed. 2005, 44: 6345 -
13b
Buchwald SL.Rainka MP.Aye Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5821 -
13c
Yun J.Lee D. Tetrahedron Lett. 2004, 45: 5415 -
14a
Togni A.Breutel C.Schnyder A.Spindler F.Landert H.Tijani A. J. Am. Chem. Soc. 1994, 116: 4062 -
14b
Blaser H.-U.Brieden W.Pugin B.Spindler F.Studer M.Togni A. Top. Catal. 2002, 19: 3 -
16a
Lipshutz BH.Servesko JM.Taft BR. J. Am. Chem. Soc. 2004, 126: 8352 -
16b
Hughes G.Kimura M.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 11253 - 17
Fleming I.Kindon ND. J. Chem. Soc., Perkin Trans. 1 1995, 303
References
Catalog # L14561. PMHS purchased from Acros does not give the same results.
15See http://www.solvias.com/.