Insertion of carbenoids into Cp-H bonds of ferrocenes: An enantioselective-catalytic entry to planar-chiral ferrocenes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 22, 1997, Pages 2456-2458

  Siegel, Stephan ^a   Schmalz, Hans Günther ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Asymmetric catalysis; C H activation; Carbene complexes; Chirality; Sandwich complexes

Indexed keywords

EID: 0031438505     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199724561     Document Type: Article

References (49)

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3. See for instance a) H.-G. Schmalz, A. Schwarz, G. Dürner, Tetrahedron Lett. 1994, 35, 6861; b) H.-G. Schmalz, E. Hessler, J. W. Bats, G. Dürner, ibid. 1994, 35, 4543; c) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597; Angew. Chem. Int. Ed. Engl. 1995, 34, 2383; d) H.-G. Schmalz, K. Schellhaas, ibid. 1996, 108, 2277 and 1996, 35, 2146.
4. See for instance a) H.-G. Schmalz, A. Schwarz, G. Dürner, Tetrahedron Lett. 1994, 35, 6861; b) H.-G. Schmalz, E. Hessler, J. W. Bats, G. Dürner, ibid. 1994, 35, 4543; c) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597; Angew. Chem. Int. Ed. Engl. 1995, 34, 2383; d) H.-G. Schmalz, K. Schellhaas, ibid. 1996, 108, 2277 and 1996, 35, 2146.
5. See for instance a) H.-G. Schmalz, A. Schwarz, G. Dürner, Tetrahedron Lett. 1994, 35, 6861; b) H.-G. Schmalz, E. Hessler, J. W. Bats, G. Dürner, ibid. 1994, 35, 4543; c) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597; Angew. Chem. Int. Ed. Engl. 1995, 34, 2383; d) H.-G. Schmalz, K. Schellhaas, ibid. 1996, 108, 2277 and 1996, 35, 2146.
6. See for instance a) H.-G. Schmalz, A. Schwarz, G. Dürner, Tetrahedron Lett. 1994, 35, 6861; b) H.-G. Schmalz, E. Hessler, J. W. Bats, G. Dürner, ibid. 1994, 35, 4543; c) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597; Angew. Chem. Int. Ed. Engl. 1995, 34, 2383; d) H.-G. Schmalz, K. Schellhaas, ibid. 1996, 108, 2277 and 1996, 35, 2146.
7. See for instance a) H.-G. Schmalz, A. Schwarz, G. Dürner, Tetrahedron Lett. 1994, 35, 6861; b) H.-G. Schmalz, E. Hessler, J. W. Bats, G. Dürner, ibid. 1994, 35, 4543; c) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597; Angew. Chem. Int. Ed. Engl. 1995, 34, 2383; d) H.-G. Schmalz, K. Schellhaas, ibid. 1996, 108, 2277 and 1996, 35, 2146.
8. See for instance a) H.-G. Schmalz, A. Schwarz, G. Dürner, Tetrahedron Lett. 1994, 35, 6861; b) H.-G. Schmalz, E. Hessler, J. W. Bats, G. Dürner, ibid. 1994, 35, 4543; c) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597; Angew. Chem. Int. Ed. Engl. 1995, 34, 2383; d) H.-G. Schmalz, K. Schellhaas, ibid. 1996, 108, 2277 and 1996, 35, 2146.
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10. Planar-chiral ferrocene derivatives are especially important in the field of enantioselective catalysis; see for instance a) T. Hayashi in ref. [2], pp. 105-142; b) Y. Butsugan, S. Araki, M. Watanabe in ref. [2], pp. 143-169; c) A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475, and references therein.
11. Planar-chiral ferrocene derivatives are especially important in the field of enantioselective catalysis; see for instance a) T. Hayashi in ref. [2], pp. 105-142; b) Y. Butsugan, S. Araki, M. Watanabe in ref. [2], pp. 143-169; c) A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475, and references therein.
12. Planar-chiral ferrocene derivatives are especially important in the field of enantioselective catalysis; see for instance a) T. Hayashi in ref. [2], pp. 105-142; b) Y. Butsugan, S. Araki, M. Watanabe in ref. [2], pp. 143-169; c) A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475, and references therein.
13. Planar-chiral ferrocene derivatives are especially important in the field of enantioselective catalysis; see for instance a) T. Hayashi in ref. [2], pp. 105-142; b) Y. Butsugan, S. Araki, M. Watanabe in ref. [2], pp. 143-169; c) A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475, and references therein.
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49. 3. The absolute configuration of the cyclization product (14 oder ent-14) was not established; the enantiomeric excess was determined with HPLC using a Daicel Chiralcel OJ column.