Catalytic asymmetric alkylation of nucleophiles: Asymmetric synthesis of α-alkylated amino acids

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 23, 1997, Pages 2635-2637

  Trost, Barry M ^a   Ariza, Xavier ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Alkylations; Amino acids; Asymmetric catalysis; Palladium; Peptidomimetics

Indexed keywords

EID: 0031573960     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199726351     Document Type: Article

References (58)

1. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
2. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
3. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
4. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
5. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
6. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
7. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
8. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
9. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
10. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
11. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
12. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
13. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
14. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
15. Selected reviews: a) D. F. Veber, R. M. Freidinger, Trends Neurosci. 1995, 8, 392; b) A Textbook of Drug Design and Development (Eds.: P. Krosgaard-Larsen, H. Bundgaard), Harwood Academic Publishers, Chur, 1991; c) G. Jung, A. G. Beck-Sickinger, Angew. Chem. 1992, 104, 375; Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383; d) P. Balaram, Curr. Opin. Struct. Biol. 1992, 2, 845-851; e) P. W. Schiller in Medicinal Chemistry for the 21st Century (Ed.: C. G. Wermuth), Oxford Blackwell Scientific Publications, Oxford, 1992, Chapter 15; f) A. Giannis,T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267; g) V. J. Hruby in Peptides Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium (Eds.: R. S. Hudges, J. A. Smith), Escom Science, 1993, pp. 3-17; h) Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. E. Wolff), Wiley, New York, 1995; i) M. Goodman, S. Ro in ref.[1h], Chapter 20, pp. 803-861; j) J. G. Cannon in ref.[1h]. Chapter 19, pp. 783-801; k) A. Muscale, G. L. Kenyon in ref.[1h]. Chapter 18, pp. 733-782; l) G. R. Marshall in ref.[1h]. Chapter 15, pp. 573-660; m) B. Veerapandian in ref.[1h]. Chapter 10, pp. 303-348.
16. Selected reviews: R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; H. Heimgartner, Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264; I. Ojima, Acc. Chem. Res. 1995, 28, 383-389; Y. Ohfune, S.-H. Moon, M. Horikawa, Pure Appl. Chem. 1996, 68, 645-648; T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
17. Selected reviews: R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; H. Heimgartner, Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264; I. Ojima, Acc. Chem. Res. 1995, 28, 383-389; Y. Ohfune, S.-H. Moon, M. Horikawa, Pure Appl. Chem. 1996, 68, 645-648; T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
18. Selected reviews: R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; H. Heimgartner, Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264; I. Ojima, Acc. Chem. Res. 1995, 28, 383-389; Y. Ohfune, S.-H. Moon, M. Horikawa, Pure Appl. Chem. 1996, 68, 645-648; T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
19. Selected reviews: R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; H. Heimgartner, Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264; I. Ojima, Acc. Chem. Res. 1995, 28, 383-389; Y. Ohfune, S.-H. Moon, M. Horikawa, Pure Appl. Chem. 1996, 68, 645-648; T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
20. Selected reviews: R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; H. Heimgartner, Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264; I. Ojima, Acc. Chem. Res. 1995, 28, 383-389; Y. Ohfune, S.-H. Moon, M. Horikawa, Pure Appl. Chem. 1996, 68, 645-648; T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
21. Selected reviews: R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; H. Heimgartner, Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264; I. Ojima, Acc. Chem. Res. 1995, 28, 383-389; Y. Ohfune, S.-H. Moon, M. Horikawa, Pure Appl. Chem. 1996, 68, 645-648; T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
22. Selected reviews: R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; H. Heimgartner, Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264; I. Ojima, Acc. Chem. Res. 1995, 28, 383-389; Y. Ohfune, S.-H. Moon, M. Horikawa, Pure Appl. Chem. 1996, 68, 645-648; T. Wirth, Angew. Chem. 1997, 109, 235-237; Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
23. J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995.
24. D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. 1996, 108, 2880-2921; Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748.
25. D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. 1996, 108, 2880-2921; Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748.
26. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
27. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
28. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
29. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
30. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
31. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
32. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
33. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
34. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
35. For recent reports, see U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941 -954; U Kazmaier, J. Org. Chem. 1996, 67, 3694-3699; V. Ferey, L. Toupet, T. Le Gall, C. Mioskowski, Angew. Chem. 1996, 103, 475-477; Angew. Chem. Int. Ed. Engl. 1996, 35, 430-432; D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086 B. Westermann, I. Gedrath, Synlett 1996, 665-666; L. M. Harwood, K. J. Vines, M. G. B. Drew, ibid. 1996, 1051-1053; D. Obrecht, C. Abrecht, M. Altorfer, U. Bohdal, A. Grieder, M. Kleber, P. Pfyffer, K. Müller, Helv. Chim. Acta 1996, 79, 1315-1337; B. G. M. Burgaud, D. C. Horwell, A. Padova, M. C. Pritchard, Tetrahedron 1996, 52, 13035-13050; C. Cativiela, M. D. Diazde-Villegas, J. A. Gálvez, Y. Lapeņa, ibid. 1997, 53, 5891-5898.
36. Allylated derivatives: T. M. Zydowsky, J. F. Dellaria, H. N. Nellans, J. Org. Chem. 1988, 53, 5607-5616; S. Thaisrivongs, D. T. Pals, S. R. Turner, L. T. Kroll, J. Med. Chem. 1988, 37, 1369-1376; M. W. Holladay, A. M. Nadzan, J. Org. Chem. 1991, 56, 3900-3905; A. B. Smith III; T. P. Keenan, R. C. Holcomb, P. A. Sprengeler, M. C. Guzman, J. L. Wood, P. J. Carroll, R. Hirschmann, J. Am. Chem. Soc. 1992, 114, 10672-10674; C. Bisang, C. Weber, J. Inglis, C. A. Schiffer, W. F. van Gunsteren, I. Jelesarov, H. R. Bosshard, J. A. Robinson, ibid. 1995, 777, 7904-7915; R. Badorrey, CCativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Y.Lapeňa, Tetrahedron: Asymmetry 1997, 8, 331-317.
37. Allylated derivatives: T. M. Zydowsky, J. F. Dellaria, H. N. Nellans, J. Org. Chem. 1988, 53, 5607-5616; S. Thaisrivongs, D. T. Pals, S. R. Turner, L. T. Kroll, J. Med. Chem. 1988, 37, 1369-1376; M. W. Holladay, A. M. Nadzan, J. Org. Chem. 1991, 56, 3900-3905; A. B. Smith III; T. P. Keenan, R. C. Holcomb, P. A. Sprengeler, M. C. Guzman, J. L. Wood, P. J. Carroll, R. Hirschmann, J. Am. Chem. Soc. 1992, 114, 10672-10674; C. Bisang, C. Weber, J. Inglis, C. A. Schiffer, W. F. van Gunsteren, I. Jelesarov, H. R. Bosshard, J. A. Robinson, ibid. 1995, 777, 7904-7915; R. Badorrey, CCativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Y.Lapeňa, Tetrahedron: Asymmetry 1997, 8, 331-317.
38. Allylated derivatives: T. M. Zydowsky, J. F. Dellaria, H. N. Nellans, J. Org. Chem. 1988, 53, 5607-5616; S. Thaisrivongs, D. T. Pals, S. R. Turner, L. T. Kroll, J. Med. Chem. 1988, 37, 1369-1376; M. W. Holladay, A. M. Nadzan, J. Org. Chem. 1991, 56, 3900-3905; A. B. Smith III; T. P. Keenan, R. C. Holcomb, P. A. Sprengeler, M. C. Guzman, J. L. Wood, P. J. Carroll, R. Hirschmann, J. Am. Chem. Soc. 1992, 114, 10672-10674; C. Bisang, C. Weber, J. Inglis, C. A. Schiffer, W. F. van Gunsteren, I. Jelesarov, H. R. Bosshard, J. A. Robinson, ibid. 1995, 777, 7904-7915; R. Badorrey, CCativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Y.Lapeňa, Tetrahedron: Asymmetry 1997, 8, 331-317.
39. Allylated derivatives: T. M. Zydowsky, J. F. Dellaria, H. N. Nellans, J. Org. Chem. 1988, 53, 5607-5616; S. Thaisrivongs, D. T. Pals, S. R. Turner, L. T. Kroll, J. Med. Chem. 1988, 37, 1369-1376; M. W. Holladay, A. M. Nadzan, J. Org. Chem. 1991, 56, 3900-3905; A. B. Smith III; T. P. Keenan, R. C. Holcomb, P. A. Sprengeler, M. C. Guzman, J. L. Wood, P. J. Carroll, R. Hirschmann, J. Am. Chem. Soc. 1992, 114, 10672-10674; C. Bisang, C. Weber, J. Inglis, C. A. Schiffer, W. F. van Gunsteren, I. Jelesarov, H. R. Bosshard, J. A. Robinson, ibid. 1995, 777, 7904-7915; R. Badorrey, CCativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Y.Lapeňa, Tetrahedron: Asymmetry 1997, 8, 331-317.
40. Allylated derivatives: T. M. Zydowsky, J. F. Dellaria, H. N. Nellans, J. Org. Chem. 1988, 53, 5607-5616; S. Thaisrivongs, D. T. Pals, S. R. Turner, L. T. Kroll, J. Med. Chem. 1988, 37, 1369-1376; M. W. Holladay, A. M. Nadzan, J. Org. Chem. 1991, 56, 3900-3905; A. B. Smith III; T. P. Keenan, R. C. Holcomb, P. A. Sprengeler, M. C. Guzman, J. L. Wood, P. J. Carroll, R. Hirschmann, J. Am. Chem. Soc. 1992, 114, 10672-10674; C. Bisang, C. Weber, J. Inglis, C. A. Schiffer, W. F. van Gunsteren, I. Jelesarov, H. R. Bosshard, J. A. Robinson, ibid. 1995, 777, 7904-7915; R. Badorrey, CCativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Y.Lapeňa, Tetrahedron: Asymmetry 1997, 8, 331-317.
41. Allylated derivatives: T. M. Zydowsky, J. F. Dellaria, H. N. Nellans, J. Org. Chem. 1988, 53, 5607-5616; S. Thaisrivongs, D. T. Pals, S. R. Turner, L. T. Kroll, J. Med. Chem. 1988, 37, 1369-1376; M. W. Holladay, A. M. Nadzan, J. Org. Chem. 1991, 56, 3900-3905; A. B. Smith III; T. P. Keenan, R. C. Holcomb, P. A. Sprengeler, M. C. Guzman, J. L. Wood, P. J. Carroll, R. Hirschmann, J. Am. Chem. Soc. 1992, 114, 10672-10674; C. Bisang, C. Weber, J. Inglis, C. A. Schiffer, W. F. van Gunsteren, I. Jelesarov, H. R. Bosshard, J. A. Robinson, ibid. 1995, 777, 7904-7915; R. Badorrey, CCativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Y. Lapeňa, Tetrahedron: Asymmetry 1997, 8, 331-317.
42. a) Ref.[7c], Chapter 2, and references therein;
43. b) ref.[7c], Chapter-4, pp. 207-212. Chapter 7,pp. 333-342;
44. R. Noyori, Asymmetric Catalysis inOrganic Synthesis, Wiley, New York, 1994.
45. M. Sawamura, M. Sudoh, Y. Ito, J. Am. Chem. Soc.1996, 118, 3309-3310.
46. J. C. Fiaud, A. H. De Gournay, M. Larchvéque, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; Y. Ito, M. Sawamura, M. Matsuoka, Y. Matsumoto, T.Hayashi, Tetrahedron Lett. 1987, 28, 4849-4852; J.-P. Genêt, S. Juge, S. Achi, S. Mallart, J. R. Montes, G. Levif, Tetrahedron 1988, 44, 5263-5275; T. Hayashi,K. Kanehira, T. Hagihara, M. Kumada, J. Org.Chem. 1988, 53, 113-120; M. Sawamura, Y. Na- kayama, W.-M. Tang, Y. Ito, ibid. 1996, 61, 9090-9096.
47. J. C. Fiaud, A. H. De Gournay, M. Larchvéque, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; Y. Ito, M. Sawamura, M. Matsuoka, Y. Matsumoto, T.Hayashi, Tetrahedron Lett. 1987, 28, 4849-4852; J.-P. Genêt, S. Juge, S. Achi, S. Mallart, J. R. Montes, G. Levif, Tetrahedron 1988, 44, 5263-5275; T. Hayashi,K. Kanehira, T. Hagihara, M. Kumada, J. Org.Chem. 1988, 53, 113-120; M. Sawamura, Y. Na- kayama, W.-M. Tang, Y. Ito, ibid. 1996, 61, 9090-9096.
48. J. C. Fiaud, A. H. De Gournay, M. Larchvéque, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; Y. Ito, M. Sawamura, M. Matsuoka, Y. Matsumoto, T.Hayashi, Tetrahedron Lett. 1987, 28, 4849-4852; J.-P. Genêt, S. Juge, S. Achi, S. Mallart, J. R. Montes, G. Levif, Tetrahedron 1988, 44, 5263-5275; T. Hayashi,K. Kanehira, T. Hagihara, M. Kumada, J. Org.Chem. 1988, 53, 113-120; M. Sawamura, Y. Na- kayama, W.-M. Tang, Y. Ito, ibid. 1996, 61, 9090-9096.
49. J. C. Fiaud, A. H. De Gournay, M. Larchvéque, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; Y. Ito, M. Sawamura, M. Matsuoka, Y. Matsumoto, T.Hayashi, Tetrahedron Lett. 1987, 28, 4849-4852; J.-P. Genêt, S. Juge, S. Achi, S. Mallart, J. R. Montes, G. Levif, Tetrahedron 1988, 44, 5263-5275; T. Hayashi,K. Kanehira, T. Hagihara, M. Kumada, J. Org.Chem. 1988, 53, 113-120; M. Sawamura, Y. Na- kayama, W.-M. Tang, Y. Ito, ibid. 1996, 61, 9090-9096.
50. J. C. Fiaud, A. H. De Gournay, M. Larchvéque, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; Y. Ito, M. Sawamura, M. Matsuoka, Y. Matsumoto, T.Hayashi, Tetrahedron Lett. 1987, 28, 4849-4852; J.-P. Genêt, S. Juge, S. Achi, S. Mallart, J. R. Montes, G. Levif, Tetrahedron 1988, 44, 5263-5275; T. Hayashi,K. Kanehira, T. Hagihara, M. Kumada, J. Org.Chem. 1988, 53, 113-120; M. Sawamura, Y. Na- kayama, W.-M. Tang, Y. Ito, ibid. 1996, 61, 9090-9096.
51. B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364.
52. Review on azlactones: A. K. Mukerjce, Heterocycles 1987, 26, 1077-1097; Y. S. Rao in Oxazoles (The Chemistry of Heterocyclic Compounds), Vol. 45 (Ed.: I. J. Turchi), Wiley, 1986, Chapter 3, pp. 361 615.
53. Review on azlactones: A. K. Mukerjce, Heterocycles 1987, 26, 1077-1097; Y. S. Rao in Oxazoles (The Chemistry of Heterocyclic Compounds), Vol. 45 (Ed.: I. J. Turchi), Wiley, 1986, Chapter 3, pp. 361 615.
54. The d.r. and ee values were established by means of HPLC with a Chiralcel OD column with heptane/2-propanol mixtures as eluent.
55. H. Dahn, J. A. Garbarino, C. O'Murchu, Helv. Chim. Acta. 1970, 53, 1370-1378.
56. B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1994, 116, 4089-4090.
57. B. M. Trost, J. Vercauteren, Tetrahedron Lett. 1985, 26, 131-134.
58. B. M. Trost, C.-B. Lee, J. M. Weiss, J. Am. Chem. Soc. 1995, 117, 7247-7248.