Investigations of a nucleophilic alaninol synthon derived from serine

Journal of the American Chemical Society

Volumn 121, Issue 33, 1999, Pages 7509-7516

  Sibi, Mukund P ^a   Rutherford, Drew ^a   Renhowe, Paul A ^a   Li, Biqin ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2 OXAZOLIDONYL)METHYLTRIPHENYLPHOSPHINYL IODIDE; ALKENE; SERINE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL BINDING; CHIRALITY; SYNTHESIS;

EID: 0033603875     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9906249     Document Type: Article

References (96)

1. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
2. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
3. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
4. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
5. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
6. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
7. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
8. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
9. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
10. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
11. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
12. General: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989; Chapter 2 and references therein. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Nucleophilic synthons: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164. (c) Daddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. (d) Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459. (e) Malan, C.; Morin, C. Synlett 1996, 167. (f) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (g) Blanchard, P.; El Kortbi, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319. Electrophilic synthons: (h) Dureault, A.; Tranchepain I.; Depezay, J.-C. J. Org. Chem. 1989, 54, 5324. (i) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073. Radical alaninol synthons: (j) Maria, E. J.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A.; Robert-Gero, M. Tetrahedron Lett. 1994, 35, 3301.
13. Nucleophilic synthons: (a) Baldwin, J. E.; Moloney, M. G.; North, M J. Chem. Soc., Perkin Trans. 1 1989, 833. Aspartate Derivatives: (b) Baldwin, J. E.; Moloney, M. G.; North, M. Tetrahedron 1989, 45, 6309. Electrophilic alanine/alaninol synthons. Aziridines: (c) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Sulfamidates: (d) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881. Radical alanine synthon: (e) Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1986, 1339.
14. Nucleophilic synthons: (a) Baldwin, J. E.; Moloney, M. G.; North, M J. Chem. Soc., Perkin Trans. 1 1989, 833. Aspartate Derivatives: (b) Baldwin, J. E.; Moloney, M. G.; North, M. Tetrahedron 1989, 45, 6309. Electrophilic alanine/alaninol synthons. Aziridines: (c) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Sulfamidates: (d) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881. Radical alanine synthon: (e) Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1986, 1339.
15. Nucleophilic synthons: (a) Baldwin, J. E.; Moloney, M. G.; North, M J. Chem. Soc., Perkin Trans. 1 1989, 833. Aspartate Derivatives: (b) Baldwin, J. E.; Moloney, M. G.; North, M. Tetrahedron 1989, 45, 6309. Electrophilic alanine/alaninol synthons. Aziridines: (c) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Sulfamidates: (d) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881. Radical alanine synthon: (e) Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1986, 1339.
16. Nucleophilic synthons: (a) Baldwin, J. E.; Moloney, M. G.; North, M J. Chem. Soc., Perkin Trans. 1 1989, 833. Aspartate Derivatives: (b) Baldwin, J. E.; Moloney, M. G.; North, M. Tetrahedron 1989, 45, 6309. Electrophilic alanine/alaninol synthons. Aziridines: (c) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Sulfamidates: (d) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881. Radical alanine synthon: (e) Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1986, 1339.
17. Nucleophilic synthons: (a) Baldwin, J. E.; Moloney, M. G.; North, M J. Chem. Soc., Perkin Trans. 1 1989, 833. Aspartate Derivatives: (b) Baldwin, J. E.; Moloney, M. G.; North, M. Tetrahedron 1989, 45, 6309. Electrophilic alanine/alaninol synthons. Aziridines: (c) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Sulfamidates: (d) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881. Radical alanine synthon: (e) Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1986, 1339.
18. (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772 and references therein. For slight variants see:
19. (b) Beaulieu, P. L.; Schiller, P. W. Tetrahedron Lett. 1988, 29, 2019.
20. (c) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021.
21. Selected examples of reactions of zinc reagents see: (a) Jackson, R. F. W.; James, K.; Wythes, M. J.; Wood., A. J. Chem. Soc., Chem. Commun. 1989, 644. (b) Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397. (c) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1996, 862. (d) Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815.
22. Selected examples of reactions of zinc reagents see: (a) Jackson, R. F. W.; James, K.; Wythes, M. J.; Wood., A. J. Chem. Soc., Chem. Commun. 1989, 644. (b) Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397. (c) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1996, 862. (d) Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815.
23. Selected examples of reactions of zinc reagents see: (a) Jackson, R. F. W.; James, K.; Wythes, M. J.; Wood., A. J. Chem. Soc., Chem. Commun. 1989, 644. (b) Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397. (c) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1996, 862. (d) Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815.
24. Selected examples of reactions of zinc reagents see: (a) Jackson, R. F. W.; James, K.; Wythes, M. J.; Wood., A. J. Chem. Soc., Chem. Commun. 1989, 644. (b) Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397. (c) Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett 1996, 862. (d) Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815.
25. Sulfones: (a) Sasaki, N. A.; Hashimoto, C.; Potier, P. Tetrahedron Lett. 1987, 28, 6069. (b) Sasaki, N. A.; Hashimoto, C.; Pauly, R. Tetrahedron Lett. 1989, 30, 1943.
26. Sulfones: (a) Sasaki, N. A.; Hashimoto, C.; Potier, P. Tetrahedron Lett. 1987, 28, 6069. (b) Sasaki, N. A.; Hashimoto, C.; Pauly, R. Tetrahedron Lett. 1989, 30, 1943.
27. Electrophilic alaninol synthons. β-lactones: (a) Arnold, L. D.; May, R. G.; Vederas, J. C. J. Am. Chem. Soc. 1988, 110, 2237 and references therein. (b) Arnold, L. D.; Drover, J. C. G.; Vederas, J. C. J. Am. Chem. Soc. 1987, 109, 4649.
28. Electrophilic alaninol synthons. β-lactones: (a) Arnold, L. D.; May, R. G.; Vederas, J. C. J. Am. Chem. Soc. 1988, 110, 2237 and references therein. (b) Arnold, L. D.; Drover, J. C. G.; Vederas, J. C. J. Am. Chem. Soc. 1987, 109, 4649.
29. Electrophilic synthons: (a) Bajgrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigiere, Ch.; Viallefont, Ph. Tetrahedron 1985, 41, 1833. (b) El Marini, A.; Roumestant, M. L.; Viallefont, P.; Razafindrambou, D.; Bonato, M.; Follet, M. Synthesis 1992, 1104. (c) Atmani, A.; El Hallaoui, A.; El Hajji, S.; Roumestant, M. L.; Viallefont, P. Synth. Commun. 1991, 21, 2383.
30. Electrophilic synthons: (a) Bajgrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigiere, Ch.; Viallefont, Ph. Tetrahedron 1985, 41, 1833. (b) El Marini, A.; Roumestant, M. L.; Viallefont, P.; Razafindrambou, D.; Bonato, M.; Follet, M. Synthesis 1992, 1104. (c) Atmani, A.; El Hallaoui, A.; El Hajji, S.; Roumestant, M. L.; Viallefont, P. Synth. Commun. 1991, 21, 2383.
31. Electrophilic synthons: (a) Bajgrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigiere, Ch.; Viallefont, Ph. Tetrahedron 1985, 41, 1833. (b) El Marini, A.; Roumestant, M. L.; Viallefont, P.; Razafindrambou, D.; Bonato, M.; Follet, M. Synthesis 1992, 1104. (c) Atmani, A.; El Hallaoui, A.; El Hajji, S.; Roumestant, M. L.; Viallefont, P. Synth. Commun. 1991, 21, 2383.
32. Nucleophilic synthons: (a) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115. Electrophilic synthon: (c) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675. Radical synthon: (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063.
33. Nucleophilic synthons: (a) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115. Electrophilic synthon: (c) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675. Radical synthon: (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063.
34. Nucleophilic synthons: (a) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115. Electrophilic synthon: (c) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675. Radical synthon: (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063.
35. Nucleophilic synthons: (a) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115. Electrophilic synthon: (c) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675. Radical synthon: (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063.
36. For a preliminary account of this work see: Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 31, 7407.
37. (a) Barrett, G. C., Ed. Chemistry and Biochemistry of the Amino Acids; Chapman and Hall: London, U.K., 1985.
38. (b) Wagner, I.; Musso, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 816.
39. (c) Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, J. J. Am. Chem. Soc. 1988, 110, 1547.
40. (a) Chang, M. N. T.; Walsh, C. J. Am. Chem. Soc. 1980, 102, 7368.
41. (b) Silverman, R. B. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC Press: Boca Raton, FL, 1988.
42. (c) Walsh, C. Tetrahedron 1982, 58, 871.
43. (d) Rando, R. R. Science 1974, 185, 320.
44. (d) Andrews, M. D.; O'Callaghan, K. A.; Vederas, J. C. Tetrahedron 1997, 53, 8295.
45. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
46. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
47. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
48. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
49. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
50. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
51. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
52. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
53. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
54. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
55. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
56. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
57. For the synthesis of β,γ-unsaturated amino acids see review: Havlicek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365. For a recent effort in this area see: Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445 and references therein. Other selected work see: (a) Baldwin, J. E.; Adlington, R. M.; O'Niel, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852. (b) Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1991, 30, 705. (c) Castelhano, A. L.; Home, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein. (d) Angst, C. Pure Appl. Chem. 1987, 59, 373. (e) Crisp, G. T.; Glink, P. T. Tetrahedron 1992, 48, 3541. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Synthesis 1997, 747. (f) O'Donnell, M. J.; Li, M.; Bennett, W. D.; Grote, T. Tetrahedron Lett. 1994, 35, 9383. (g) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966. (h) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39. (i) Clayden, J.; Collington, E. W.; Warren, S. Tetrahedron Lett. 1993, 34, 1327. (j) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
58. Itaya, T.; Shimomichi, M.; Ozasa, M. Tetrahedron Lett. 1988, 29, 4129.
59. (a) Itaya, T.; Iida, T.; Shimuzu, S.; Mizutani, A.; Morisue, M.; Sugimoto, Y.; Tachinaka, M. Chem. Pharm. Bull. Jpn. 1993, 41, 252.
60. (b) Itaya, T.; Kanai, T.; Iida, T. Tetrahedron Lett. 1997, 38, 1979.
61. For applications of this synthon in synthesis see: (a) Refs 10a and c.
62. (b) Bertozzi, C.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092.
63. (c) Bertozzi, C.; Cook, D. G.; Kobertz, W. R.; Gonzalez-Scarano, F.; Bednarski, M. J. Am. Chem. Soc. 1992, 114, 10639.
64. Serine methyl ester hydrochloride is commercially available or it can be readily prepared in high yields from serine, thionyl chloride, and methanol (Guttmann, S.; Boissonnas, R. A. Helv. Chim. Acta 1958, 41, 1852).
65. Sibi, M. P.; Harris, B. J.; Renhowe, P. A.; Rutherford, D.; Christensen, J. W.; Li, B.; Lu, J. Organic Synth. under evaluation.
66. Koellensperger, F. G.; Hartelben, Y.; Kretzschmar, R.; Neleter, B. Ger. Patent. 2538424, 1977; Chem. Abstr. 1977, 87, 23257Z.
67. (a) Linderman, R. J.; Meyers, A. I. Tetrahedron Lett. 1983, 24, 3043.
68. (b) Refs 4a and 7a.
69. (c) Ref 3a.
70. (d) McGarvey, G. J.; Hiner, R. N.; Matsubara, Y.; Oh, T. Tetrahedron Lett. 1983, 24, 2733.
71. (e) McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943.
72. (f) Jackson, R. F. W.; James, K.; Wythes, M. J.; Wood, A. Tetrahedron Lett. 1989, 30, 5941.
73. Eyer, M.; Seebach, D. J. Am. Chem. Soc. 1985, 107, 3601 and references therein.
74. Several products from the Wittig olefination process have been convened to known compounds. See, for example, refs 10a,b and 17.
75. The reasons for the variation in stereoselectivity with changes in the base are not apparent.
76. The exact reasons for this variation in selectivity with structural modifications of the aldehydes are not apparent at this time. In an analogous series, N-protected α-amino aldehydes react with 7 to provide Z-olefins only. Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, in press.
77. (a) For comprehensive reviews see: (a) Vedejs, E.; Peterson. M. J. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 2, Chapter 1. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (c) Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993. (d) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324.
78. (a) For comprehensive reviews see: (a) Vedejs, E.; Peterson. M. J. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 2, Chapter 1. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (c) Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993. (d) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324.
79. (a) For comprehensive reviews see: (a) Vedejs, E.; Peterson. M. J. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 2, Chapter 1. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (c) Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993. (d) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324.
80. (a) For comprehensive reviews see: (a) Vedejs, E.; Peterson. M. J. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 2, Chapter 1. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (c) Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993. (d) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324.
81. For an excellent discussion on stereochemistry and mechanism of Wittig reactions using oxido ylides see: Vedejs, E.; Peterson. M. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1994, Vol. 21, Chapter 1.
82. Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217.
83. Boubia, B.; Mann, A.; Bellamy, F. D.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1990, 29, 1454.
84. For Z-selective olefinations with α-alkoxyaldehydes see: Takanashi, T.; Miyazawa, M.; Ueno, H.; Tsuji, J. Tetrahedron Lett. 1986, 27, 3881.
85. The observed high (Z)-selectivity for the glyceraldhyde acetonide is mostly due to the reactivity of the aldehyde and the irreversibility of the reaction. Formation of the alternate (E)-isomer places the rigid dioxolane ring close to bulky phosphine.
86. (a) Zhang, X.-M.; Bordwell, F. G. J. Org. Chem. 1994, 59, 6456.
87. (b) Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1994, 116, 968.
88. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
89. We believe that the major decomposition pathway is through ring opening of the ylide and nucleophilic attack at the carbamate carbonyl is minor. For an example of ring opening of an oxazolidinone by BuLi see: Mirzaei, Y. R.; Balasubramaniam, T. N.; Lefler, B. J.; Natale, N. R. J. Heterocycl. Chem. 1990, 27, 2000.
90. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185.
91. Esterification of the primary alcohol with Mosher acid see: Svatos, A.; Valterova, I.; Saman, D.; Vrkoc, J. Collect. Czech. Chem. Commun. 1990, 55, 485.
92. For selected methods for the conversion of amino alcohols to amino acids: (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (b) Pasto, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron: Asymmetry 1995, 6, 2329. (c) Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758. (d) Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196. (e) See refs 7 and 17b.
93. For selected methods for the conversion of amino alcohols to amino acids: (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (b) Pasto, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron: Asymmetry 1995, 6, 2329. (c) Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758. (d) Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196. (e) See refs 7 and 17b.
94. For selected methods for the conversion of amino alcohols to amino acids: (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (b) Pasto, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron: Asymmetry 1995, 6, 2329. (c) Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758. (d) Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196. (e) See refs 7 and 17b.
95. For selected methods for the conversion of amino alcohols to amino acids: (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (b) Pasto, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron: Asymmetry 1995, 6, 2329. (c) Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758. (d) Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196. (e) See refs 7 and 17b.
96. For selected methods for the conversion of amino alcohols to amino acids: (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559. (b) Pasto, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron: Asymmetry 1995, 6, 2329. (c) Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758. (d) Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196. (e) See refs 7 and 17b.