A practical and efficient synthesis of enantiomerically pure di-tert- butylethanediamine

Synthesis

Volumn , Issue 2, 1999, Pages 228-230

  Roland, Sylvain ^a   Mangeney, Pierre ^a   Alexakis, Alex ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Chiral 1,2 diimine; Diastereoselective addition; Grignard reagent; Hydrogenolysis; Ligand precursor

Indexed keywords

ETHYLENEDIAMINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032980393     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3391     Document Type: Article

References (27)

1. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
2. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
3. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
4. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
5. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
6. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
7. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
8. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
9. Tomioka, K. Synthesis 1990, 541. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Jacobsen, E. J. Catalytic Asymmetric Synthesis, Ed.: Ojima, VCH, 1993, p 159/179. Katsuki, T. J. Mol. Cat. 1996, 113, 87. Mukaiyama, T. Aldrichimica Acta 1996, 29, 59. Mukaiyama, T. and Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17 and 1455. Trost, B. M.; Van Vrancken, D. L. Chem. Rev. 1996, 96, 395.
10. Alexakis, A.; Mangeney, P. Advanced Asymmetric Synthesis; Stephenson, G. R., Ed.; Chapman & Hall, 1996; p 93. Barett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc. Chem. Comm. 1994, 2739.
11. Alexakis, A.; Mangeney, P. Advanced Asymmetric Synthesis; Stephenson, G. R., Ed.; Chapman & Hall, 1996; p 93. Barett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc. Chem. Comm. 1994, 2739.
12. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
13. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
14. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
15. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
16. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
17. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
18. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
19. For the diamine 1, see: Pini, D.; Iuliano, A.; Rosini, C.; Salvadori, P. Synthesis 1990, 1023. Lohray, B. B.; Ahuja, J. R., J. Chem. Soc. Chem. Comm. 1991, 95. Oi, R.; Sharpless, K. B.; Tetrahedron Lett. 1991, 32, 999. Corey, E. J.; Imwinkelried, R., Pikul, S., Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 4486. Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. For the diamine 2, see: Wieland, A.; Schlichtung, O.; Langsdorf, W. V. Z. Phys. Chem. 1926, 161, 74. Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511. Whitney, T. A. J. Org. Chem. 1980, 45, 4214.
20. Tom Dieck, H.; Dietrich, J. Chem. Ber. 1984, 117, 694.
21. Neumann, W. L.; Rogic, M. M.; Dunn, T. J. Tetrahedron Lett. 1991, 32, 5865.
22. Alvaro, J.; Grepioni, F.; Savoia, D. J. Org. Chem. 1997, 62, 4180.
23. Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
24. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
25. Rasmussen, K. G.; Thomsen, D. S.; Jørgensen, K. A. J. Chem. Soc. Perkin Trans 1 1995, 2009.
26. The yield was determined by formation and isolation of the aminal 7 from the crude mixture.
27. Anwer, M. K.; Spatda, A. F. Synthesis 1980, 929.