Generation of aziridinyllithiums from sulfinylaziridines by the ligand exchange reaction of sulfoxides with tert-butyllithium: Their properties and an application to asymmetric synthesis of α-dialkylamino acid ester

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2345-2348

  Satoh, Tsuyoshi ^a   Ozawa, Masaki ^a   Takano, Koji ^a   Kudo, Masabumi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AZIRIDINE DERIVATIVE; AZIRIDINYLLITHIUM; ESTER DERIVATIVE; LITHIUM DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; LIGAND BINDING; MOLECULAR INTERACTION;

EID: 0032537205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00150-6     Document Type: Article

References (25)

1. 1. Armarego, W. L. F. "Stereochemistry of Heterocyclic Compounds" John Wiley and Sons: New York, 1977; Part I. Deyrup, J. A. in "Small Ring Heterocycles" Hassner, A. ed.; John Wiley and Sons: New York, 1983; Part I. Kametani, T.; Honda, T. in "Advances in Heterocyclic Chemistry" Katritzky, A. R. ed.; Academic Press: Orlando, 1986; Vol. 39, p 181.
2. 1. Armarego, W. L. F. "Stereochemistry of Heterocyclic Compounds" John Wiley and Sons: New York, 1977; Part I. Deyrup, J. A. in "Small Ring Heterocycles" Hassner, A. ed.; John Wiley and Sons: New York, 1983; Part I. Kametani, T.; Honda, T. in "Advances in Heterocyclic Chemistry" Katritzky, A. R. ed.; Academic Press: Orlando, 1986; Vol. 39, p 181.
3. 1. Armarego, W. L. F. "Stereochemistry of Heterocyclic Compounds" John Wiley and Sons: New York, 1977; Part I. Deyrup, J. A. in "Small Ring Heterocycles" Hassner, A. ed.; John Wiley and Sons: New York, 1983; Part I. Kametani, T.; Honda, T. in "Advances in Heterocyclic Chemistry" Katritzky, A. R. ed.; Academic Press: Orlando, 1986; Vol. 39, p 181.
4. 2. Satoh, T. Chem. Rev. 1996, 96, 3303.
5. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
6. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
7. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
8. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
9. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
10. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
11. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
12. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
13. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
14. 3. Only three reports have been published so far concerning nonstabilized aziridinyl anions other than our works: Atkinson, R. S.; Kelly, B. J. Tetrahedron Lett. 1989, 30, 2703. Vedejs, E.; Moss, W. J. Am. Chem. Soc. 1993, 115, 1607. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941. Some papers for stabilized aziridinyl anions: Tarburton, P.; Chung, A.; Badger, R. C.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 295. Tarburton, P.; Wall, D. K.; Cromwell, N. H. J. Heterocycl. Chem. 1976, 13, 411 Gaillot, J.-M; Gelas-Mialhe, Y.; Vessiere, R. Can. J. Chem. 1979, 57, 1958. Seebach, D.; Haner, R. Chem. Lett. 1987, 49. Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676. Coutrot, P.; Elgadt, A.; Grison, C. Heterocycles 1989, 28, 1179. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M J. Org. Chem. 1994, 59, 276.
15. 4. a) Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 4093.
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17. 5. Reviews on the ligand exchange reaction of sulfoxides: Oae, S. "Reviews on Heteroatom Chemistry" 1991, 4, 195 MYU, Tokyo. Satoh, T. J. Syn. Org. Chem. Jpn. 1996, 54, 481.
18. 5. Reviews on the ligand exchange reaction of sulfoxides: Oae, S. "Reviews on Heteroatom Chemistry" 1991, 4, 195 MYU, Tokyo. Satoh, T. J. Syn. Org. Chem. Jpn. 1996, 54, 481.
19. 6. Satoh, T.; Horiguchi, K. Tetrahedron Lett. 1995, 36, 8235.
20. 7. THF was distilled from diphenylketyl.
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25. 10. HPLC analysis of racemic 11 using a chiral column (Daisel Chiralpak AD, 10% 2-isopropanol in hexane, flow rate 0.5 m1/min) showed clear separation of both enantiomers. The enantiomeric purity of (-)-11 was found to be over 99%.