Unexpected metal base-dependent inversion of the enantioselectivity in the asymmetric synthesis of α-amino acids using phase-transfer catalysts derived from cinchonidine

Tetrahedron Asymmetry

Volumn 13, Issue 20, 2002, Pages 2181-2185

  Mazón, Patricia ^a   Chinchilla, Rafael ^a   Nájera, Carmen ^a   Guillena, Gabriela ^b   Kreiter, Rob ^b   Klein Gebbink, Robertus J M ^b   Van Koten, Gerard ^b  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE EARTH METAL; ALPHA AMINO ACID; BENZYL BROMIDE; BENZYL DERIVATIVE; CINCHONIDINE; ESTER DERIVATIVE; GLYCINE DERIVATIVE; METAL; N (DIPHENYLMETHYLENE)GLYCINE ISOPROPYL ESTER; POTASSIUM HYDROXIDE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 0037131665     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00611-0     Document Type: Article

References (65)

1. Dehmlow E.V., Dehmlow S.S. Phase Transfer Catalysis. 3rd ed. 1993;VCH, Weinheim.
2. (b) Starks C.M., Liotta C.L., Halpern M. Phase Transfer Catalysis - Fundamentals, Applications and Industrial Perspectives; Chapman and Hall: New York, 1994;
3. (c) Phase Transfer Catalysis; Halpern, M. E., Ed.; American Chemical Society, Symposium Series 659; ACS: Washington, DC, 1997.
4. For reviews, see: (a) Martyres, D. Synlett 1999, 1508-1508; (b) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (c) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; VCH: New York, 2000; pp. 389-411; (e) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-13; (f) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961-998.
5. For reviews, see: (a) Martyres, D. Synlett 1999, 1508-1508; (b) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (c) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; VCH: New York, 2000; pp. 389-411; (e) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-13; (f) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961-998.
6. For reviews, see: (a) Martyres, D. Synlett 1999, 1508-1508; (b) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (c) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; VCH: New York, 2000; pp. 389-411; (e) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-13; (f) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961-998.
7. For reviews, see: (a) Martyres, D. Synlett 1999, 1508-1508; (b) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (c) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; VCH: New York, 2000; pp. 389-411; (e) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-13; (f) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961-998.
8. For reviews, see: (a) Martyres, D. Synlett 1999, 1508-1508; (b) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (c) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; VCH: New York, 2000; pp. 389-411; (e) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-13; (f) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961-998.
9. For reviews, see: (a) Martyres, D. Synlett 1999, 1508-1508; (b) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (c) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697; (d) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; VCH: New York, 2000; pp. 389-411; (e) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-13; (f) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961-998.
10. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
11. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
12. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
13. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
14. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
15. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
16. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
17. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
18. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
19. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
20. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
21. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
22. For recent examples, see: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259; (b) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959-2962; (c) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301; (d) Arai, S.; Shioiri, T. Tetrahedron 2002, 58, 1407-1413; (e) Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498; (f) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630; (g) Lygo, B.; To, C. M. Tetrahedron Lett. 2001, 42, 1343-1346; (h) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846; (i) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273-1276; (j) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934; (k) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547; (l) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729; (m) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216.
23. Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 121:1999;6519-6520.
24. Ooi T., Tayama E., Doda K., Takeuchi M., Maruoka K. Synlett. 2000;1500-1502.
25. Ooi T., Takeuchi M., Kameda M., Maruoka K. J. Am. Chem. Soc. 122:2000;5228-5229.
26. Manabe K. Tetrahedron Lett. 39:1998;5807-5810.
27. Manabe K. Tetrahedron. 54:1998;14456-14476.
28. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Chesnokov A.A., Larionov A.V., Parmár V.S., Kumar R., Kagan H.B. Tetrahedron: Asymmetry. 9:1998;851-857.
29. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Chesnokov A.A., Larionov A.V., Singh I., Parmár V.S., Vyskocil S., Kagan H.B. J. Org. Chem. 65:2000;7041-7048.
30. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Vyskocil S., Kagan H.B. Tetrahedron: Asymmetry. 10:1999;1723-1728.
31. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Larionov O.V., Harutyunyan S.R., Vyskocil S., North M., Kagan H.B. Angew Chem., Int. Ed. 40:2001;1948-1951.
32. Casas J., Nájera C., Sansano J.M., González J., Saá J.M., Vega M. Tetrahedron: Asymmetry. 12:2001;699-702.
33. Belokon' Y.N., North M., Kublitski V.S., Ikonnikov N.S., Krasik P.E., Maleev V.L. Tetrahedron Lett. 40:1999;6105-6108.
34. Belokon' Y.N., Davies R.G., North M. Tetrahedron Lett. 41:2000;7245-7248.
35. O'Donnell M.J., Bennett W.D., Wu S. J. Am. Chem. Soc. 111:1989;2353-2355.
36. Lipkowitz K.B., Cavanaugh M.W., Baker B., O'Donnell M.J. J. Org. Chem. 56:1991;5181-5192.
37. O'Donnell M.J., Wu S. Tetrahedron: Asymmetry. 3:1992;591-594.
38. O'Donnell M.J., Wu S., Huffman J.C. Tetrahedron. 50:1994;4507-4518.
39. O'Donnell M.J., Delgado F., Hostettler R., Schwesinger R. Tetrahedron Lett. 39:1998;8775-8778.
40. O'Donnell M.J., Delgado F., Pottorf R. Tetrahedron. 55:1999;6347-6362.
41. Lygo B., Wainwright P.G. Tetrahedron Lett. 38:1997;8595-8598.
42. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;1385-1388.
43. Lygo B. Tetrahedron Lett. 40:1999;1389-1392.
44. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;8671-8674.
45. Lygo B., Crosby J., Lowdon T.R., Wainwright P.G. Tetrahedron. 57:2001;2391-2402.
46. Lygo B., Crosby J., Lowdon T.R., Peterson J.A., Wainwright P.G. Tetrahedron. 57:2001;2403-2409.
47. Corey E.J., Xu F., Noe M.C. J. Am. Chem. Soc. 119:1997;12414-12415.
48. Corey E.J., Noe M.C., Xu F. Tetrahedron Lett. 39:1998;5347-5350.
49. Corey E.J., Bo Y., Busch-Peterson J. J. Am. Chem. Soc. 120:1998;13000-13001.
50. Jew S., Jeong B., Yoo M., Huh H., Park H. Chem. Commun. 2001;1244-1245.
51. Chinchilla R., Mazón P., Nájera C. Tetrahedron: Asymmetry. 13:2002;927-931.
52. Park H., Jeong B.-S., Yoo M.-S., Lee J.-H., Park M., Lee Y.-J., Kim M.-J., Jew S. Angew Chem., Int. Ed. 41:2002;3036-3038.
53. Park H., Jeong B., Yoo M., Park M., Huh H., Jew S. Tetrahedron Lett. 42:2001;4645-4648.
54. Zhang Z., Wang Y., Zhen W., Hodge P. React. Funct. Polym. 41:1999;37-43.
55. Chinchilla R., Mazón P., Nájera C. Tetrahedron: Asymmetry. 11:2000;3277-3281.
56. 3) δ 22.7, 25.3, 26.4, 37.9, 50.2, 60.0, 62.2, 65.5, 66.7, 70.0, 104.7, 112.9, 118.0, 119.9, 123.2, 123.7, 127.7, 127.95, 128.0, 128.7, 128.9, 129.1, 136.2, 137.0, 149.0, 159.3.
57. Reimann E. Chem. Ber. 102:1969;2881-2888.
58. 3) δ 22.6, 25.1, 26.7, 37.7, 51.1, 59.6, 62.1, 66.1, 70.2, 104.2, 113.0, 118.3, 119.8, 124.5, 125.1, 127.8, 127.9, 128.4, 129.1, 129.8, 130.2, 132.4, 136.1, 136.4, 139.8, 148.4, 149.3, 159.7.
59. 3) δ 22.2, 24.8, 26.6, 29.6, 37.7, 50.9, 53.4, 59.4, 61.4, 62.4, 70.1, 72.4, 104.6, 112.8, 118.5, 119.2, 127.6, 127.7, 127.8, 128.0, 128.3, 128.5, 129.2, 129.4, 129.5, 132.3, 135.2, 136.0, 136.3, 136.4, 137.6, 150.2, 159.6.
60. Prepared in 80% overall yield by reaction of glycine with thionyl chloride in the presence of iso-propanol (see: Patel, R.; Price, S. J. Org. Chem. 1965, 30, 3575-3576), followed by treatment of the crude with benzophenone imine (see: O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663-2666).
61. Prepared in 80% overall yield by reaction of glycine with thionyl chloride in the presence of iso-propanol (see: Patel, R.; Price, S. J. Org. Chem. 1965, 30, 3575-3576), followed by treatment of the crude with benzophenone imine (see: O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663-2666).
62. Chirasil-LVal (Chrompack), 1 min 85°C, 2°C/min to 180°C. Reference racemic samples were prepared using tetrabutylammonium bromide as phase-transfer catalyst.
63. . Obtained after hydrolysis of the imine with 2 M aq. HCl and further reaction with trifluoroacetic anhydride. See: Oppolzer W., Moretti R., Zhou C. Helv. Chim. Acta. 77:1994;2363-2380.
64. Dehmlow E.V., Knufinke V. Liebigs Ann. Chem. 1992;283-285.
65. 3) δ 22.4, 25.2, 26.4, 37.9, 50.5, 55.5, 60.4, 62.4, 65.0, 67.1, 102.2, 111.6, 117.9, 119.8, 122.9, 123.6, 127.5, 128.5, 128.8, 129.4, 136.0, 144.9, 146.8, 149.2, 160.5.