Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to enones with new peptidyl phosphane ligands

Tetrahedron Asymmetry

Volumn 14, Issue 24, 2003, Pages 3823-3826

  Breit, Bernhard ^a   Laungani, Andy Ch ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; LIGAND; PEPTIDE DERIVATIVE; REAGENT; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CONJUGATE; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 0345170096     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.002     Document Type: Article

References (38)

1. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
2. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
3. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
4. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
5. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
6. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
7. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
8. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
9. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
10. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
11. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
12. General reviews: (a) Posner, G. H. Org. React. 1972, 19, 1; (b) Yamamoto, Y. Angew. Chem. 1986, 98, 945; (c) Lipshutz, B. H.; Sengupta, Z. Org. React. 1992, 41, 135; (d) Organocopper Reagents - A Practical Approach, Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; (e) Krause, N.; Gerold, A. Angew. Chem. 1997, 109, 194; Angew. Chem., Int. Ed. Engl. 1997, 36, 186. Conjugate addition: (f) Kozlowski, J. A. Comp. Org. Synth. 1991, 4, 169; (g) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771; (h) Krause, N. Kontakte (Darmstadt), 1993, 1, 3; (i) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, 1995; Vol. E21b, 2041. For applications towards total synthesis of prostaglandines: (j) Noyori, R.; Suzuki, M. Angew. Chem. 1984, 96, 854-882; Angew. Chem., Int. Ed. Engl. 1984, 23, 847-875.
13. Substrate control: (a) Breit, B.; Demel, P. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 6, p. 188. Reagent control: Ref. 1g; (b) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 7, p. 224.
14. Substrate control: (a) Breit, B.; Demel, P. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 6, p. 188. Reagent control: Ref. 1g; (b) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 7, p. 224.
15. Breit B., Demel P. Tetrahedron. 56:2000;2833 Breit, B. Angew. Chem. 1998, 110, 535; Angew. Chem., Int. Ed. Engl. 1998, 37, 525.
16. Breit B., Demel P. Tetrahedron. 56:2000;2833 Breit, B. Angew. Chem. 1998, 110, 535; Angew. Chem., Int. Ed. Engl. 1998, 37, 525.
17. Breit B. Chem. Eur. J. 6:2000;1519.
18. For other types of peptidyl modified phosphane ligands for asymmetric catalysis, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523; (b) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091-2094.
19. For other types of peptidyl modified phosphane ligands for asymmetric catalysis, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523; (b) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091-2094.
20. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
21. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
22. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
23. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
24. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
25. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
26. Hu X., Chen H., Zhang X., Angew. Chem., Int. Ed., 1999, 38, 3518-3521.
27. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
28. For reviews, see: (a) Alexakis, A. Eur. J. Org. Chem. 2002, 3221; Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. See also: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; (b) Strangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510; (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105; (d) Alexakis, A.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811-1813; (e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521; (f) Yamanoi, Y.; Imamoto, T. J. Am. Chem. Soc. 1999, 64, 2988-2989; (g) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
29. For a similar combinatorial approach to chiral sulfonamide ligands, see: (a) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388; (b) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628; (c) Chataigner, I.; Gennari, C.; Piarulli, U.; Ceccarelli, S. Angew. Chem., Int. Ed. Engl. 2000, 39, 916-918.
30. For a similar combinatorial approach to chiral sulfonamide ligands, see: (a) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388; (b) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628; (c) Chataigner, I.; Gennari, C.; Piarulli, U.; Ceccarelli, S. Angew. Chem., Int. Ed. Engl. 2000, 39, 916-918.
31. For a similar combinatorial approach to chiral sulfonamide ligands, see: (a) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388; (b) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628; (c) Chataigner, I.; Gennari, C.; Piarulli, U.; Ceccarelli, S. Angew. Chem., Int. Ed. Engl. 2000, 39, 916-918.
32. Hird, W.; Hoveyda, A. H. Angew. Chem. 2003, 115, 1314; Angew. Chem., Int. Ed. Engl. 2003, 42, 1276.
33. Mizutani H., Degrado S.J., Hoveyda A.H. J. Am. Chem. Soc. 124:2002;779-780.
34. Degrado S.J., Mizutani H., Hoveyda A.H. J. Am. Chem. Soc. 123:2001;755-756.
35. 3 and the Z-deprotection, see: Ueda, T.; Saito, M.; Kato, T.; Izumiya, N. Bull. Chem. Soc. Jpn. 1983, 56, 568-572.
36. 4P: C, 69.48; H, 6.80; N, 5.40. Found: C, 69.22; H, 6.67; N, 5.14.
37. Alexakis A., Benhaim C.B., Rosset S., Humam M. J. Am. Chem. Soc. 124:2002;5262.
38. 4 to give the 1,4-addition products.