(S)-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) acetic acid as a solid supported chiral auxiliary in the asymmetric synthesis of β2-homoarylglycines

Tetrahedron Asymmetry

Volumn 14, Issue 9, 2003, Pages 1223-1228

  Akkari, Rhalid ^a   Calmès, Monique ^a   Di Malta, Delphine ^a   Escale, Françoise ^a   Martinez, Jean ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

(3 HYDROXY 4,4 DIMETHYL 2 OXOPYRROLIDIN 1 YL)ACETIC ACID; ACETIC ACID DERIVATIVE; GLYCINE DERIVATIVE; KETENE DERIVATIVE; RESIN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; STEREOCHEMISTRY;

EID: 0037414485     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00178-2     Document Type: Article

References (57)

1. Thompson L.A., Ellman J.A. Chem. Rev. 96:1996;555-600.
2. Dolle R.E., Nelson K.H. J. Comb. Chem. 1:1999;235-282.
3. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
4. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
5. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
6. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
7. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
8. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
9. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
10. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
11. For recent examples of synthetic solid-supported reagent or catalyst see: Altava, B.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Pozo, O.; Salvator, R. V. Eur. J. Org. Chem. 1999, 2263-2267; Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Polym. 1999, 41, 37-43; Dong, C.; Zhang, J. L.; Zheng, W. H.; Zhang, L. F.; Yu, Z. L.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2000, 11, 2449-2454; Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296; Mandoli, A.; Pini, D.; Agostini, A.; Salvadori, P. Tetrahedron: Asymmetry 2000, 11, 4039-4042; Chinchilla, R.; Mazon, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277-3281; Altava, B.; Burguete, M. I.; Collado, M.; Garcia-Verdugo, E.; Luis, S. V.; Salvador, R. V.; Vincent, M. J. Tetrahedron Lett. 2001, 42, 1673-1675; Hallman, K.; Moberg, C. Tetrahedron: Asymmetry 2001, 12, 1475-1478; Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983-986.
12. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
13. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
14. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
15. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
16. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
17. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
18. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
19. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
20. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
21. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
22. For recent applications of synthetic solid-supported auxiliary, see: Moon, H.-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088-6089; Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918; Shuttleworth, S. J.; Allin, S. M. Tetrahedron Lett. 1996, 37, 8023-8026; Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777-8780; Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655-2658; Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4936; Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265-1269; Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621-8625; Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445; Faita, G.; Paio, A.; Quadrelli, P.; Rancatiand, F.; Seneci, P. Tetrahedron 2001, 57, 8313-8322; Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381-2383.
23. For recent examples of stereoselective reactions on solid support, see: Ojima, I.; Tsai, C.-Y.; Zhang, Z. Tetrahedron Lett. 1994, 35, 5785-5788; Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851-6852; Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247; Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587; Panek, J. S.; Zhu, B. J. Am. Chem. Soc. 1997, 119, 12022-12023; Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910.
24. For recent examples of stereoselective reactions on solid support, see: Ojima, I.; Tsai, C.-Y.; Zhang, Z. Tetrahedron Lett. 1994, 35, 5785-5788; Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851-6852; Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247; Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587; Panek, J. S.; Zhu, B. J. Am. Chem. Soc. 1997, 119, 12022-12023; Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910.
25. For recent examples of stereoselective reactions on solid support, see: Ojima, I.; Tsai, C.-Y.; Zhang, Z. Tetrahedron Lett. 1994, 35, 5785-5788; Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851-6852; Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247; Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587; Panek, J. S.; Zhu, B. J. Am. Chem. Soc. 1997, 119, 12022-12023; Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910.
26. For recent examples of stereoselective reactions on solid support, see: Ojima, I.; Tsai, C.-Y.; Zhang, Z. Tetrahedron Lett. 1994, 35, 5785-5788; Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851-6852; Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247; Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587; Panek, J. S.; Zhu, B. J. Am. Chem. Soc. 1997, 119, 12022-12023; Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910.
27. For recent examples of stereoselective reactions on solid support, see: Ojima, I.; Tsai, C.-Y.; Zhang, Z. Tetrahedron Lett. 1994, 35, 5785-5788; Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851-6852; Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247; Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587; Panek, J. S.; Zhu, B. J. Am. Chem. Soc. 1997, 119, 12022-12023; Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910.
28. For recent examples of stereoselective reactions on solid support, see: Ojima, I.; Tsai, C.-Y.; Zhang, Z. Tetrahedron Lett. 1994, 35, 5785-5788; Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851-6852; Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246-12247; Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587; Panek, J. S.; Zhu, B. J. Am. Chem. Soc. 1997, 119, 12022-12023; Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910.
29. Akkari R., Calmès M., Mai N., Rolland M., Martinez J. J. Org. Chem. 66:2001;5859-5965.
30. Juaristi E. Enantioselective synthesis of β-Aminoacids. 1997;1-66 Wiley-VLH, John Wiley & Sons, New York.
31. Cole D.C. Tetrahedron. 50:1994;9517-9582.
32. Juaristi E. Aldrichimica Acta. 27:(1):1994;3-11.
33. Sewald N. Amino Acids. 11:1996;397-408.
34. Cardillo G., Tomasini C. Chem. Soc. Rev. 1996;117-128.
35. Abdel-Magid A.F., Cohen J.H., Marayanoff C.A. Curr. Med. Chem. 6:1999;955-970.
36. Juaristi E., López-Ruiz H. Curr. Med. Chem. 6:1999;983-1004.
37. Liu M., Sibi M.P. Tetrahedron. 58:2002;7991-8035. and references cited therein.
38. For example, see: Scott, V. R.; Boehme, R.; Matthews, T. R. Antimicrob. Agents Chemother. 1988, 32, 1154-1160; Rowinsky, E. K.; Donehower, R. C. Pharmacol. Ther. 1991, 52, 35-41; Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-168.
39. For example, see: Scott, V. R.; Boehme, R.; Matthews, T. R. Antimicrob. Agents Chemother. 1988, 32, 1154-1160; Rowinsky, E. K.; Donehower, R. C. Pharmacol. Ther. 1991, 52, 35-41; Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-168.
40. For example, see: Scott, V. R.; Boehme, R.; Matthews, T. R. Antimicrob. Agents Chemother. 1988, 32, 1154-1160; Rowinsky, E. K.; Donehower, R. C. Pharmacol. Ther. 1991, 52, 35-41; Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-168.
41. For example, see: Shinagawa, S.; Kanamaru, T.; Harada, S.; Asai, M.; Okazaki, H. J. Med. Chem. 1987, 30, 1458-1463; Kawabata, N.; Inamoto, Y.; Sakane, K.; Iwamoto, T.; Hashimoto, S. J. Antibiot. 1992, 45, 909-912.
42. For example, see: Shinagawa, S.; Kanamaru, T.; Harada, S.; Asai, M.; Okazaki, H. J. Med. Chem. 1987, 30, 1458-1463; Kawabata, N.; Inamoto, Y.; Sakane, K.; Iwamoto, T.; Hashimoto, S. J. Antibiot. 1992, 45, 909-912.
43. 2-substituted compounds involves diastereoselective alkylation of an enolate derived from β-alanine; for example, see: Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557; Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1993, 4, 229-238; Akssira, M.; Boumzebra, M.; Kasmi, H.; Roumestant M. L.; Viallefont, P. Amino Acids 1994, 7, 79-81; D'Souza, A. A.; Motevalli, M.; Robinson A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1995, 1-2; Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246; Seebach, D.; Boog, A.; Schweizer, W. B. Eur. J. Org. Chem. 1999, 335-360.
44. 2-substituted compounds involves diastereoselective alkylation of an enolate derived from β-alanine; for example, see: Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557; Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1993, 4, 229-238; Akssira, M.; Boumzebra, M.; Kasmi, H.; Roumestant M. L.; Viallefont, P. Amino Acids 1994, 7, 79-81; D'Souza, A. A.; Motevalli, M.; Robinson A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1995, 1-2; Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246; Seebach, D.; Boog, A.; Schweizer, W. B. Eur. J. Org. Chem. 1999, 335-360.
45. 2-substituted compounds involves diastereoselective alkylation of an enolate derived from β-alanine; for example, see: Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557; Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1993, 4, 229-238; Akssira, M.; Boumzebra, M.; Kasmi, H.; Roumestant M. L.; Viallefont, P. Amino Acids 1994, 7, 79-81; D'Souza, A. A.; Motevalli, M.; Robinson A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1995, 1-2; Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246; Seebach, D.; Boog, A.; Schweizer, W. B. Eur. J. Org. Chem. 1999, 335-360.
46. 2-substituted compounds involves diastereoselective alkylation of an enolate derived from β-alanine; for example, see: Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557; Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1993, 4, 229-238; Akssira, M.; Boumzebra, M.; Kasmi, H.; Roumestant M. L.; Viallefont, P. Amino Acids 1994, 7, 79-81; D'Souza, A. A.; Motevalli, M.; Robinson A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1995, 1-2; Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246; Seebach, D.; Boog, A.; Schweizer, W. B. Eur. J. Org. Chem. 1999, 335-360.
47. 2-substituted compounds involves diastereoselective alkylation of an enolate derived from β-alanine; for example, see: Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557; Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1993, 4, 229-238; Akssira, M.; Boumzebra, M.; Kasmi, H.; Roumestant M. L.; Viallefont, P. Amino Acids 1994, 7, 79-81; D'Souza, A. A.; Motevalli, M.; Robinson A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1995, 1-2; Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246; Seebach, D.; Boog, A.; Schweizer, W. B. Eur. J. Org. Chem. 1999, 335-360.
48. 2-substituted compounds involves diastereoselective alkylation of an enolate derived from β-alanine; for example, see: Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557; Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1993, 4, 229-238; Akssira, M.; Boumzebra, M.; Kasmi, H.; Roumestant M. L.; Viallefont, P. Amino Acids 1994, 7, 79-81; D'Souza, A. A.; Motevalli, M.; Robinson A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1995, 1-2; Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246; Seebach, D.; Boog, A.; Schweizer, W. B. Eur. J. Org. Chem. 1999, 335-360.
49. 2-substituted compounds involves diastereoselective alkylation of an enolate derived from β-alanine; for example, see: Juaristi, E.; Quintana, D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557; Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1993, 4, 229-238; Akssira, M.; Boumzebra, M.; Kasmi, H.; Roumestant M. L.; Viallefont, P. Amino Acids 1994, 7, 79-81; D'Souza, A. A.; Motevalli, M.; Robinson A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1995, 1-2; Juaristi, E.; Quintana, D.; Balderas, M.; García-Pérez, E. Tetrahedron: Asymmetry 1996, 7, 2233-2246; Seebach, D.; Boog, A.; Schweizer, W. B. Eur. J. Org. Chem. 1999, 335-360.
50. Calmès M., Escale F. Tetrahedron: Asymmetry. 9:1998;2845-2850.
51. Calmès M., Escale F., Glot C., Rolland M., Martinez J. Eur. J. Org. Chem. 2000;2459-2466.
52. Rink H. Tetrahedron Lett. 28:1987;3787-3790.
53. Bernatowicz M.S., Daniels S.B., Kôster H. Tetrahedron Lett. 30:1989;4645-4648.
54. Tidwell T. Ketenes, Wiley-Interscience Publication. 1995;299 John Wiley & Sons, New York. and 642.
55. 11 and probably due to a low stability of the intermediates involved, a rapid chromatography on silica gel of the crude esters 7b-d was necessary to obtain pure compounds.
56. 2 and then the benzhydrylamine bond was cleaved using the conventional method.
57. 15 and diastereomerically enriched compounds.