Asymmetric Hydrosilylation of Styrenes by Use of New Chiral ­Phosphoramidites

Xinsheng Li; Jianan Song; Dongcheng Xu; Lichun Kong

doi:10.1055/s-2008-1032199

PAPER

Asymmetric Hydrosilylation of Styrenes by Use of New Chiral Phosphoramidites

Xinsheng Li*, Jianan Song, Dongcheng Xu, Lichun Kong
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua 321004, P. R. of China
Fax: +86(579)82282610; e-Mail: sky33@zjnu.cn;

Abstract

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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

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References

<A NAME="RF16807SS-1A">1a</A> Itoh K. Catalytic Asymmetric Synthesis 2nd ed.: Wiley-VCH; New York: 2000.

<A NAME="RF16807SS-1B">1b</A> Gibson SE. Rudd M. Adv. Synth. Catal. 2007, 349: 781

<A NAME="RF16807SS-2">2</A> Tamao K. Ishida N. Tanaka T. Kumada M. Organometallics 1983, 2: 1694

<A NAME="RF16807SS-3A">3a</A> Kitayama K. Uozumi Y. Hayashi T. J. Chem. Soc., Chem. Commun. 1995, 1533

<A NAME="RF16807SS-3B">3b</A> Uozumi Y. Hayashi T. J. Am. Chem. Soc. 1991, 113: 9887

<A NAME="RF16807SS-3C">3c</A> Uozumi Y. Hayashi T. Tetrahedron Lett. 1993, 34: 2335

<A NAME="RF16807SS-3D">3d</A> Kitayawa K. Tsuji H. Uozumi Y. Hayashi T. Tetrahedron Lett. 1996, 37: 4169

<A NAME="RF16807SS-3E">3e</A> Han JW. Tokunaga N. Hayashi T. J. Am. Chem. Soc. 2001, 123: 12915

<A NAME="RF16807SS-3F">3f</A> Shimada T. Mukaide K. Shinohara A. Han JW. Hayashi T. J. Am. Chem. Soc. 2002, 124: 1584

<A NAME="RF16807SS-3G">3g</A> Hayashi T. Hirate S. Kitayama K. Tsuji H. Torii A. Uozumi Y. J. Org. Chem. 2001, 66: 1441

<A NAME="RF16807SS-3H">3h</A> Uozumi Y. Kitayama K. Hayashi T. Yanagi K. Fukuyo E. Bull. Chem. Soc. Jpn. 1995, 68: 713

<A NAME="RF16807SS-3I">3i</A> Hayashi T. Catal. Today 2000, 62: 3

<A NAME="RF16807SS-4A">4a</A> Pedersen HL. Johannsen M. Chem. Commun. 1999, 2517

<A NAME="RF16807SS-4B">4b</A> Pedersen HL. Johannsen M. J. Org. Chem. 2002, 67: 7982

<A NAME="RF16807SS-5">5</A> Jensen JF. Svendsen BY. la Cour TV. Pedersen HL. Johannsen M. J. Am. Chem. Soc. 2002, 124: 4558

<A NAME="RF16807SS-6">6</A> 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:

<A NAME="RF16807SS-7A">7a</A> ebesta R. Pizzuti MG. Minnaard AJ. Feringa BL. Adv. Synth. Catal. 2007, 349: 1931

<A NAME="RF16807SS-7B">7b</A> Polet D. Alexakis A. Tissot-Croset K. Corminboeuf C. Ditrich K. Chem. Eur. J. 2006, 12: 3596

<A NAME="RF16807SS-7C">7c</A> Graening T. Hartwig JF. J. Am. Chem. Soc. 2005, 127: 17192

<A NAME="RF16807SS-7D">7d</A> Welter C. Dahnz A. Brunner B. Streiff S. Dübon P. Helmchen G. Org. Lett. 2005, 7: 1239

<A NAME="RF16807SS-8A">8a</A> Betti M. Org. Synth. Coll. Vol. I 1941, 381

<A NAME="RF16807SS-8B">8b</A> Dong Y. Li R. Lu J. Xu X. Wang X. Hu Y. J. Org. Chem. 2005, 70: 8617

<A NAME="RF16807SS-9A">9a</A> Cimarelli C. Mazzanti A. Palmieri G. Volpini E. J. Org. Chem. 2001, 66: 4759

<A NAME="RF16807SS-9B">9b</A> Lu J. Xu X. Wang C. He J. Hu Y. Hu H. Tetrahedron Lett. 2002, 43: 8367

<A NAME="RF16807SS-9C">9c</A> Cimarelli C. Palmieri G. Volpini E. Tetrahedron: Asymmetry 2002, 13: 2417

<A NAME="RF16807SS-9D">9d</A> Palmieri G. Tetrahedron: Asymmetry 2000, 11: 3361

<A NAME="RF16807SS-9E">9e</A> Cardellicchio C. Ciccarella G. Naso F. Perna F. Tortorella P. Tetrahedron 1999, 55: 14685

<A NAME="RF16807SS-9F">9f</A> 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

<A NAME="RF16807SS-9G">9g</A> Ji J.-X. Qiu L.-Q. Yip CW. Chan ASC. J. Org. Chem. 2003, 68: 1589

<A NAME="RF16807SS-10">10</A> Ji J.-X. Wu J. Au-Yeung TT.-L. Yip C.-W. Haynes RK. Chan ASC. J. Org. Chem. 2005, 70: 1093

<A NAME="RF16807SS-11">11</A> Wang Y. Li X. Ding K. Tetrahedron: Asymmetry 2002, 13: 1291

<A NAME="RF16807SS-12A">12a</A> Wang X. Dong Y. Sun J. Xu X. Li R. Hu Y. J. Org. Chem. 2005, 70: 1897

<A NAME="RF16807SS-12B">12b</A> Periasamy M. Reddy MN. Anwar S. Tetrahedron: Asymmetry 2004, 15: 1809

<A NAME="RF16807SS-13">13</A> Doucet H. Fernandez E. Layzell TP. Brown JB. Chem. Eur. J. 2001, 5: 1320

Asymmetric Hydrosilylation of Styrenes by Use of New Chiral ­Phosphoramidites

Asymmetric Hydrosilylation of Styrenes by Use of New Chiral Phosphoramidites