Lateral stereocontrol using π-allylmolybdenum systems: The use of methyl substitution to effect conformational control leading to high levels of stereoselectivity

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2890-2896

  Pearson, Anthony J ^a   Neagu, Irina B ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; MOLYBDENUM;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; HYDROXYLATION; STEREOCHEMISTRY;

EID: 0033574605     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9900376     Document Type: Article

References (15)

1. 2Cp complexes, see: Vong, W. J.; Peng, S. M.; Lin, S. H.; Lin, W. J.; Liu, R. S. J. Am. Chem. Soc. 1991, 113, 573.
2. 2Cp complexes, see: Vong, W. J.; Peng, S. M.; Lin, S. H.; Lin, W. J.; Liu, R. S. J. Am. Chem. Soc. 1991, 113, 573.
3. 2Cp complexes, see: Vong, W. J.; Peng, S. M.; Lin, S. H.; Lin, W. J.; Liu, R. S. J. Am. Chem. Soc. 1991, 113, 573.
4. Tietze, L. F.; Eicher, T. Syntheses and Transformations of Functional Groups. In Reactions and Syntheses; University Science Books: Mill Valley, CA, 1989; Chapter G, pp 102-104.
5. Tate, D. P.; Knipple, W. R.; Augl, J. M. Inorg. Chem. 1962, 1, 433-434.
6. Pearson, A. J.; Schoffers, E. Organometallics 1997, 16, 5365-5367.
7. Mancuso, A. J.; Huang, S. L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
8. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773-2776.
9. Boden, R. M. Synthesis 1975, 784.
10. Ward, Y. D.; Villanueva, L. A.; Allred, G. D.; Payne, S. C.; Semones, M. A.; Liebeskind, L. S. Organometallics 1995, 14, 4132-4156.
11. Mitsunobu, O. Synthesis 1981, 1-28.
12. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943-3946. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255.
13. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943-3946. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255.
14. We are grateful to Professor A. Alan Pinkerton at the University of Toledo for X-ray structure determination on complex 25. Owing to problems of twinning in the crystal, structural data of publishable quality could not be obtained. Nevertheless, the key structural feature, i.e., the stereochemistry of the secondary alcohol relative to the π-allylmolybdenum system, could be elucidated.
15. Pearson, A. J.; Douglas, A. R. Organometallics 1998, 17, 1446-1448.