The Ups and Downs of Allylpalladium Complexes in Catalysis

Synlett

Volumn 1996, Issue 8, 1996, Pages 705-710

  Williams, Jonathan M J ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000273585     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5505     Document Type: Article

References (72)

1. Loughborough is pronounced "Luffburra" although alternative versions have been heard on occasion across the world: "Lowburrow" (US), "Logborg" (Ger), and my own favourite - Loogabarooga (Aus).
2. For general reviews on palladium catalysed allylic substitution reacions, see; Godleski, S. A. in Comprehensive Organic Synthesis, Eds. Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, 4, 585. Consiglio, G.; Waymouth, R. Chem. Rev. 1989, 89, 257. Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173. For reviews dealing with the stereocontrol of palladium catalysed allylic substitution reactions, see; Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; Hayashi, T. in Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993, Ed. Ojima, I.
3. For general reviews on palladium catalysed allylic substitution reacions, see; Godleski, S. A. in Comprehensive Organic Synthesis, Eds. Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, 4, 585. Consiglio, G.; Waymouth, R. Chem. Rev. 1989, 89, 257. Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173. For reviews dealing with the stereocontrol of palladium catalysed allylic substitution reactions, see; Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; Hayashi, T. in Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993, Ed. Ojima, I.
4. For general reviews on palladium catalysed allylic substitution reacions, see; Godleski, S. A. in Comprehensive Organic Synthesis, Eds. Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, 4, 585. Consiglio, G.; Waymouth, R. Chem. Rev. 1989, 89, 257. Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173. For reviews dealing with the stereocontrol of palladium catalysed allylic substitution reactions, see; Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; Hayashi, T. in Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993, Ed. Ojima, I.
5. For general reviews on palladium catalysed allylic substitution reacions, see; Godleski, S. A. in Comprehensive Organic Synthesis, Eds. Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, 4, 585. Consiglio, G.; Waymouth, R. Chem. Rev. 1989, 89, 257. Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173. For reviews dealing with the stereocontrol of palladium catalysed allylic substitution reactions, see; Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; Hayashi, T. in Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993, Ed. Ojima, I.
6. For general reviews on palladium catalysed allylic substitution reacions, see; Godleski, S. A. in Comprehensive Organic Synthesis, Eds. Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, 4, 585. Consiglio, G.; Waymouth, R. Chem. Rev. 1989, 89, 257. Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173. For reviews dealing with the stereocontrol of palladium catalysed allylic substitution reactions, see; Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; Hayashi, T. in Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993, Ed. Ojima, I.
7. Several research groups had already reported this approach. For early examples, see ref 4 and Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. Okada, Y.; Minami, T.; Umezu, Y.; Nishikawa, S.; Mori, R.; Nakayama, Y. Tetrahedron: Asymmetry, 1991, 2, 667. Okada, Y.; Minami, T.; Sasaki, Y.; Umezu, Y.; Yamaguchi, M. Tetrahedron Lett., 1990, 31, 3905. Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron Lett., 1990, 31, 5049.
8. Several research groups had already reported this approach. For early examples, see ref 4 and Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. Okada, Y.; Minami, T.; Umezu, Y.; Nishikawa, S.; Mori, R.; Nakayama, Y. Tetrahedron: Asymmetry, 1991, 2, 667. Okada, Y.; Minami, T.; Sasaki, Y.; Umezu, Y.; Yamaguchi, M. Tetrahedron Lett., 1990, 31, 3905. Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron Lett., 1990, 31, 5049.
9. Several research groups had already reported this approach. For early examples, see ref 4 and Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. Okada, Y.; Minami, T.; Umezu, Y.; Nishikawa, S.; Mori, R.; Nakayama, Y. Tetrahedron: Asymmetry, 1991, 2, 667. Okada, Y.; Minami, T.; Sasaki, Y.; Umezu, Y.; Yamaguchi, M. Tetrahedron Lett., 1990, 31, 3905. Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron Lett., 1990, 31, 5049.
10. Several research groups had already reported this approach. For early examples, see ref 4 and Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. Okada, Y.; Minami, T.; Umezu, Y.; Nishikawa, S.; Mori, R.; Nakayama, Y. Tetrahedron: Asymmetry, 1991, 2, 667. Okada, Y.; Minami, T.; Sasaki, Y.; Umezu, Y.; Yamaguchi, M. Tetrahedron Lett., 1990, 31, 3905. Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron Lett., 1990, 31, 5049.
11. Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191.
12. Åkermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zetterberg, K. Organometallics 1984, 3, 679.
13. Åkermark, B.; Krakenberger, B.; Hansson, S.; Vitagliano, A. Organometallics 1987, 6, 620
14. In fact, it will be the relative rate of nucleophilc addition to either of these complexes which determines the stereochemical outcome, not necessarily their relative abundance.
15. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
16. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
17. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
18. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
19. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
20. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
21. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
22. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
23. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
24. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
25. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
26. Rhodium catalysed hydrosilylation: Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. Balavoine, G.; Clinet, J. C.; Lellouche, I. Tetrahedron Lett. 1989, 30, 514. Cyclopropanation: Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Lewis acid catalysts: Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
27. Ligands 7 and 8 are not impossible to make by these routes, and in fact have subsequently been reported by other researchers (see refs 15 and 16).
28. The direct conversion of a nitrile into an oxazoline is known: Witte, H.; Seeliger, W. Justus Liebigs Ann. Chem. 1974, 68, 996. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173. This is a one step reaction if you buy valinol. However, valinol is easily prepared by the reduction of valine; Giannis, A.; Sandhoff, K. Angew. Chem., Int. Ed. Engl. 1989, 28, 218. There are many alternative reduction procedures available.
29. The direct conversion of a nitrile into an oxazoline is known: Witte, H.; Seeliger, W. Justus Liebigs Ann. Chem. 1974, 68, 996. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173. This is a one step reaction if you buy valinol. However, valinol is easily prepared by the reduction of valine; Giannis, A.; Sandhoff, K. Angew. Chem., Int. Ed. Engl. 1989, 28, 218. There are many alternative reduction procedures available.
30. The direct conversion of a nitrile into an oxazoline is known: Witte, H.; Seeliger, W. Justus Liebigs Ann. Chem. 1974, 68, 996. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173. This is a one step reaction if you buy valinol. However, valinol is easily prepared by the reduction of valine; Giannis, A.; Sandhoff, K. Angew. Chem., Int. Ed. Engl. 1989, 28, 218. There are many alternative reduction procedures available.
31. Frost, C. G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 2015.
32. It is possible that the ligands sometimes only function as monodentate ligands, and this would be likely to provide very low levels of enantioselectivity, since we know that when the thienyl group is replaced by a phenyl group, very low enantioselectivities (<5%ee) are obtained in the palladium catalysed allylic substitution reaction.
33. Coote, S. J.; Dawson, G. J.; Frost, C. G.; Williams, J. M. J. Synlett 1993, 509.
34. Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
35. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
36. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
37. By this time, Pfaltz had already reported the use of bis-oxazolines: Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143.
38. By this time, Pfaltz had already reported the use of bis-oxazolines: Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143.
39. Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793. Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans 1 1994, 2065. Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1993, 4, 1785.
40. Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793. Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans 1 1994, 2065. Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1993, 4, 1785.
41. Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793. Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans 1 1994, 2065. Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1993, 4, 1785.
42. As well as oxazolines and acetals, other functional groups have been prepared by the Loughborough group, including dihydroimidazoles, imines, cyclic aminals, etc. and these results will be published in due course.
43. Jumnah, R.; Williams, J. M. J.; Williams, A. C. Tetrahedron Lett. 1993, 34, 6619.
44. Jumnah, R.; Williams, A. C.; Williams, J. M. J. Synlett 1995, 821.
45. von Matt, P.; Loiseleur, O.; Koch, G.; Pfaltz, A.; Lefeber, C.; Feucht, T.; Helmchen, G. Tetrahedron: Asymmetry 1994, 5, 573
46. We have demonstrated that the phthalimido group may be removed without racemisation of the amino acid. R. Jumnah, A. C. Williams and J. M. J. Williams, manuscript in preparation. See also; Cleavage with sodium borohydride; Osby, J. O.; Martin, M. G.; Ganem, B.; Tetrahedron Lett. 1984, 25, 2093. Cleavage with hydrazine; Mulzer, J.; Angermann, A.; Schubert, B.; Seilz, C.; J. Org. Chem. 1986, 51, 5294.
47. We have demonstrated that the phthalimido group may be removed without racemisation of the amino acid. R. Jumnah, A. C. Williams and J. M. J. Williams, manuscript in preparation. See also; Cleavage with sodium borohydride; Osby, J. O.; Martin, M. G.; Ganem, B.; Tetrahedron Lett. 1984, 25, 2093. Cleavage with hydrazine; Mulzer, J.; Angermann, A.; Schubert, B.; Seilz, C.; J. Org. Chem. 1986, 51, 5294.
48. We have demonstrated that the phthalimido group may be removed without racemisation of the amino acid. R. Jumnah, A. C. Williams and J. M. J. Williams, manuscript in preparation. See also; Cleavage with sodium borohydride; Osby, J. O.; Martin, M. G.; Ganem, B.; Tetrahedron Lett. 1984, 25, 2093. Cleavage with hydrazine; Mulzer, J.; Angermann, A.; Schubert, B.; Seilz, C.; J. Org. Chem. 1986, 51, 5294.
49. Genêt, J. P.; Uziel, J.; Touzin, A. M.; Juge, S. Synthesis 1990, 41. Genêt, J. P.; Uziel, J.; Port, M.; Touzin, A. M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett. 1992, 33, 77 . Genêt, J. P.; Juge, S.; Achi, S.; Mallart, S.; Ruiz-Montes, J.; Levif, G. Tetrahedron 1988, 44, 5263. Genêt, J. P.; Juge, S.; Besnier, I.; Uziel, J.; Ferroud, D.; Kardos, N.; Achi, S.; Ruiz-Montes, J.; Thorimbert, S. Bull. Soc. Chim. Fr. 1990, 127, 781.
50. Genêt, J. P.; Uziel, J.; Touzin, A. M.; Juge, S. Synthesis 1990, 41. Genêt, J. P.; Uziel, J.; Port, M.; Touzin, A. M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett. 1992, 33, 77 . Genêt, J. P.; Juge, S.; Achi, S.; Mallart, S.; Ruiz-Montes, J.; Levif, G. Tetrahedron 1988, 44, 5263. Genêt, J. P.; Juge, S.; Besnier, I.; Uziel, J.; Ferroud, D.; Kardos, N.; Achi, S.; Ruiz-Montes, J.; Thorimbert, S. Bull. Soc. Chim. Fr. 1990, 127, 781.
51. Genêt, J. P.; Uziel, J.; Touzin, A. M.; Juge, S. Synthesis 1990, 41. Genêt, J. P.; Uziel, J.; Port, M.; Touzin, A. M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett. 1992, 33, 77 . Genêt, J. P.; Juge, S.; Achi, S.; Mallart, S.; Ruiz-Montes, J.; Levif, G. Tetrahedron 1988, 44, 5263. Genêt, J. P.; Juge, S.; Besnier, I.; Uziel, J.; Ferroud, D.; Kardos, N.; Achi, S.; Ruiz-Montes, J.; Thorimbert, S. Bull. Soc. Chim. Fr. 1990, 127, 781.
52. Genêt, J. P.; Uziel, J.; Touzin, A. M.; Juge, S. Synthesis 1990, 41. Genêt, J. P.; Uziel, J.; Port, M.; Touzin, A. M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett. 1992, 33, 77 . Genêt, J. P.; Juge, S.; Achi, S.; Mallart, S.; Ruiz-Montes, J.; Levif, G. Tetrahedron 1988, 44, 5263. Genêt, J. P.; Juge, S.; Besnier, I.; Uziel, J.; Ferroud, D.; Kardos, N.; Achi, S.; Ruiz-Montes, J.; Thorimbert, S. Bull. Soc. Chim. Fr. 1990, 127, 781.
53. For examples, see; Fiaud, J. C.; DeGournay, A. H.; Lachevéque, M.; Kagan, H. B. J. Organomet. Chem. 1978, 154, 175. Hayashi, T.; Kanehira, K.; Tsuchiya, H.; Kumada, M. J. Chem. Soc., Chem. Commun. 1982, 1162. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
54. For examples, see; Fiaud, J. C.; DeGournay, A. H.; Lachevéque, M.; Kagan, H. B. J. Organomet. Chem. 1978, 154, 175. Hayashi, T.; Kanehira, K.; Tsuchiya, H.; Kumada, M. J. Chem. Soc., Chem. Commun. 1982, 1162. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
55. For examples, see; Fiaud, J. C.; DeGournay, A. H.; Lachevéque, M.; Kagan, H. B. J. Organomet. Chem. 1978, 154, 175. Hayashi, T.; Kanehira, K.; Tsuchiya, H.; Kumada, M. J. Chem. Soc., Chem. Commun. 1982, 1162. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
56. P. R. Auburn, P. B. Mackenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033. P. B. MacKenzie, J. Whelan and B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046. A. Togni Tetrahedron: Asymmetry 1991, 2, 683. J. M. Brown, D. I. Hulmes and P. J. Guiry, Tetrahedron 1994, 50, 4493.
57. P. R. Auburn, P. B. Mackenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033. P. B. MacKenzie, J. Whelan and B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046. A. Togni Tetrahedron: Asymmetry 1991, 2, 683. J. M. Brown, D. I. Hulmes and P. J. Guiry, Tetrahedron 1994, 50, 4493.
58. P. R. Auburn, P. B. Mackenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033. P. B. MacKenzie, J. Whelan and B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046. A. Togni Tetrahedron: Asymmetry 1991, 2, 683. J. M. Brown, D. I. Hulmes and P. J. Guiry, Tetrahedron 1994, 50, 4493.
59. P. R. Auburn, P. B. Mackenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033. P. B. MacKenzie, J. Whelan and B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046. A. Togni Tetrahedron: Asymmetry 1991, 2, 683. J. M. Brown, D. I. Hulmes and P. J. Guiry, Tetrahedron 1994, 50, 4493.
60. Dawson, G. J.; Coote, S. J.; Williams, J. M. J. Tetrahedron Lett. 1995, 36, 41. Dawson, G. J.; Coote, S. J.; Williams, J. M. J. Tetrahedron : Asymmetry 1995, 6, 2535.
61. Dawson, G. J.; Coote, S. J.; Williams, J. M. J. Tetrahedron Lett. 1995, 36, 41. Dawson, G. J.; Coote, S. J.; Williams, J. M. J. Tetrahedron : Asymmetry 1995, 6, 2535.
62. Krapcho, A. P. Synthesis 1982, 893.
63. Sprinz, J.; Kiefer, M. Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
64. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
65. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
66. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
67. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
68. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
69. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
70. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
71. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
72. Some of the recent ligands developed for palladium catalysed asymmetric allylic substitution include; Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386. Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 1109. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4361. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc., 1994, 116, 4089. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.