Diastereoselective Additions of Chiral Vinylzinc Reagents to α-Chiral Aldehydes

Organic Letters

Volumn 6, Issue 3, 2004, Pages 445-448

  Marshall, James A ^a   Eidam, Patrick ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BROMINE DERIVATIVE; METHYLEPHEDRINE; VINYL DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHELATION; CHIRALITY; LITHIATION; STEREOCHEMISTRY;

ALDEHYDES; EPHEDRINE; LITHIUM; MAGNESIUM; MOLECULAR STRUCTURE; STEREOISOMERISM; VINYL COMPOUNDS; ZINC;

EID: 1342285487     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0363568     Document Type: Article

References (22)

1. Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085.
2. Total syntheses: Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 40, 603. Evans, D. A.; Hu, E.; Burch, J. D.; Jaeschke, G. J. Am. Chem. Soc. 2002, 124, 5654. Trost, B. M.; Gunzer, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396. Paterson, I.; Davies, R. D. M.; Heimann, A. C.; Marquez, R.; Meyer, A. Org. Lett. 2003, 5, 4477.
3. Total syntheses: Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 40, 603. Evans, D. A.; Hu, E.; Burch, J. D.; Jaeschke, G. J. Am. Chem. Soc. 2002, 124, 5654. Trost, B. M.; Gunzer, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396. Paterson, I.; Davies, R. D. M.; Heimann, A. C.; Marquez, R.; Meyer, A. Org. Lett. 2003, 5, 4477.
4. Total syntheses: Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 40, 603. Evans, D. A.; Hu, E.; Burch, J. D.; Jaeschke, G. J. Am. Chem. Soc. 2002, 124, 5654. Trost, B. M.; Gunzer, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396. Paterson, I.; Davies, R. D. M.; Heimann, A. C.; Marquez, R.; Meyer, A. Org. Lett. 2003, 5, 4477.
5. Total syntheses: Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 40, 603. Evans, D. A.; Hu, E.; Burch, J. D.; Jaeschke, G. J. Am. Chem. Soc. 2002, 124, 5654. Trost, B. M.; Gunzer, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396. Paterson, I.; Davies, R. D. M.; Heimann, A. C.; Marquez, R.; Meyer, A. Org. Lett. 2003, 5, 4477.
6. Aldehyde 1 was prepared by a route analogous to that described in Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Am. Chem. Soc. 1998, 63, 817. Full details will be disclosed in due course.
7. Wipf, P.; Lim, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1068.
8. Kitamura, M.; Suga, S.; Kawal, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
9. For a recent comprehensive review, see: Pu. L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
10. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1991, 32, 5777.
11. An intramolecular version of the reaction was employed by Oppolzer in reported syntheses of (R)-(-)-muscone and (+)-aspercilin, two relatively simple macrocylic natural products. Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607. See also: Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773.
12. An intramolecular version of the reaction was employed by Oppolzer in reported syntheses of (R)-(-)-muscone and (+)-aspercilin, two relatively simple macrocylic natural products. Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607. See also: Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773.
13. An intramolecular version of the reaction was employed by Oppolzer in reported syntheses of (R)-(-)-muscone and (+)-aspercilin, two relatively simple macrocylic natural products. Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607. See also: Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773.
14. Soai, K.; Hatanaka, T.; Yamashita, T. J. Chem. Soc., Chem. Commun. 1992, 927. Soai, K.; Shimada, C.; Takeuchi, M.; Itabashi, M. J. Chem. Soc., Chem. Commun. 1994, 567. Watanabe, M.; Komota, M.; Nishimura, M.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2193.
15. Soai, K.; Hatanaka, T.; Yamashita, T. J. Chem. Soc., Chem. Commun. 1992, 927. Soai, K.; Shimada, C.; Takeuchi, M.; Itabashi, M. J. Chem. Soc., Chem. Commun. 1994, 567. Watanabe, M.; Komota, M.; Nishimura, M.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2193.
16. Soai, K.; Hatanaka, T.; Yamashita, T. J. Chem. Soc., Chem. Commun. 1992, 927. Soai, K.; Shimada, C.; Takeuchi, M.; Itabashi, M. J. Chem. Soc., Chem. Commun. 1994, 567. Watanabe, M.; Komota, M.; Nishimura, M.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2193.
17. Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
18. Marshall, J. A.; Yu, R. H.; Perkins, J. H. J. Org. Chem. 1995, 60, 5550.
19. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. D. J. Org. Chem. 1986, 51, 2370.
20. Massad, S.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5188.
21. Ireland, R. E.; Thaisrivongs, S.; Dussalt, P. H. J. Am. Chem. Soc. 1998 110, 5768.
22. For a recent application of this transition state to alkynylzinc reagents, see Fettes, A.; Carreira, E. M. J. Org. Chem. 2003, 68, 9274.