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 2008(6): 925-931
DOI: 10.1055/s-2008-1032199
DOI: 10.1055/s-2008-1032199
PAPER
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Hydrosilylation of Styrenes by Use of New Chiral Phosphoramidites
Weitere Informationen
Received
18 September 2007
Publikationsdatum:
28. Februar 2008 (online)
Publikationsverlauf
Publikationsdatum:
28. Februar 2008 (online)

Abstract
New chiral phosphoramidites were synthesized from chiral unsymmetrical amines and BINOL in good yields. Enantioselective hydrosilylation of styrenes with trichlorosilane in the presence of palladium complexes of these ligands provided chiral silanes in medium to high yields. Oxidation of these chiral silanes with hydrogen peroxide gave the corresponding chiral secondary alcohols in up to 97% ee.
Key words
hydrosilylation - phosphoramidites - asymmetric synthesis - chiral secondary alcohols - palladium
-
1a
Itoh K. Catalytic Asymmetric Synthesis 2nd ed.: Wiley-VCH; New York: 2000. -
1b
Gibson SE.Rudd M. Adv. Synth. Catal. 2007, 349: 781 - 2
Tamao K.Ishida N.Tanaka T.Kumada M. Organometallics 1983, 2: 1694 -
3a
Kitayama K.Uozumi Y.Hayashi T. J. Chem. Soc., Chem. Commun. 1995, 1533 -
3b
Uozumi Y.Hayashi T. J. Am. Chem. Soc. 1991, 113: 9887 -
3c
Uozumi Y.Hayashi T. Tetrahedron Lett. 1993, 34: 2335 -
3d
Kitayawa K.Tsuji H.Uozumi Y.Hayashi T. Tetrahedron Lett. 1996, 37: 4169 -
3e
Han JW.Tokunaga N.Hayashi T. J. Am. Chem. Soc. 2001, 123: 12915 -
3f
Shimada T.Mukaide K.Shinohara A.Han JW.Hayashi T. J. Am. Chem. Soc. 2002, 124: 1584 -
3g
Hayashi T.Hirate S.Kitayama K.Tsuji H.Torii A.Uozumi Y. J. Org. Chem. 2001, 66: 1441 -
3h
Uozumi Y.Kitayama K.Hayashi T.Yanagi K.Fukuyo E. Bull. Chem. Soc. Jpn. 1995, 68: 713 -
3i
Hayashi T. Catal. Today 2000, 62: 3 -
4a
Pedersen HL.Johannsen M. Chem. Commun. 1999, 2517 -
4b
Pedersen HL.Johannsen M. J. Org. Chem. 2002, 67: 7982 - 5
Jensen JF.Svendsen BY.la Cour TV.Pedersen HL.Johannsen M. J. Am. Chem. Soc. 2002, 124: 4558 - 6
Guo X.-X.Xie J.-H.Hou G.-H.Shi W.-J.Wang L.-X.Zhou Q.-L. Tetrahedron: Asymmetry 2004, 15: 2231 - For asymmetric addition and allylic alkylation by unsymmetrical-amine-containing ligands, see:
-
7a
ebesta R.Pizzuti MG.Minnaard AJ.Feringa BL. Adv. Synth. Catal. 2007, 349: 1931 -
7b
Polet D.Alexakis A.Tissot-Croset K.Corminboeuf C.Ditrich K. Chem. Eur. J. 2006, 12: 3596 -
7c
Graening T.Hartwig JF. J. Am. Chem. Soc. 2005, 127: 17192 -
7d
Welter C.Dahnz A.Brunner B.Streiff S.Dübon P.Helmchen G. Org. Lett. 2005, 7: 1239 -
8a
Betti M. Org. Synth. Coll. Vol. I 1941, 381 -
8b
Dong Y.Li R.Lu J.Xu X.Wang X.Hu Y. J. Org. Chem. 2005, 70: 8617 -
9a
Cimarelli C.Mazzanti A.Palmieri G.Volpini E. J. Org. Chem. 2001, 66: 4759 -
9b
Lu J.Xu X.Wang C.He J.Hu Y.Hu H. Tetrahedron Lett. 2002, 43: 8367 -
9c
Cimarelli C.Palmieri G.Volpini E. Tetrahedron: Asymmetry 2002, 13: 2417 -
9d
Palmieri G. Tetrahedron: Asymmetry 2000, 11: 3361 -
9e
Cardellicchio C.Ciccarella G.Naso F.Perna F.Tortorella P. Tetrahedron 1999, 55: 14685 -
9f
Liu D.-X.Zhang L.-C.Wang Q.Da C S.Xin Z.-Q.Wang R.Choi MCK.Chan ASC. Org. Lett. 2001, 3: 2733 -
9g
Ji J.-X.Qiu L.-Q.Yip CW.Chan ASC. J. Org. Chem. 2003, 68: 1589 - 10
Ji J.-X.Wu J.Au-Yeung TT.-L.Yip C.-W.Haynes RK.Chan ASC. J. Org. Chem. 2005, 70: 1093 - 11
Wang Y.Li X.Ding K. Tetrahedron: Asymmetry 2002, 13: 1291 -
12a
Wang X.Dong Y.Sun J.Xu X.Li R.Hu Y. J. Org. Chem. 2005, 70: 1897 -
12b
Periasamy M.Reddy MN.Anwar S. Tetrahedron: Asymmetry 2004, 15: 1809 - 13
Doucet H.Fernandez E.Layzell TP.Brown JB. Chem. Eur. J. 2001, 5: 1320