Chiral complexes with n-butyllithium and methylzinc: X-ray crystal structures of lithium and zinc (1R,2R,4S)-2-endo-oxido-2-exo-(o-methoxyphenyl)-1,3,3-trimethylbicyclo[2.2.1] heptane

Organometallics

Volumn 18, Issue 16, 1999, Pages 2927-2929

  Goldfuss, Bernd ^a   Khan, Saeed I ^b   Houk, K N ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5844376812     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990184u     Document Type: Article

References (43)

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11. Enantioselective additions of lithium acetylides have been employed, e.g., in the synthesis of the HIV-1 reverse transcriptase inhibitor Efavirenz: (a) Pierce, M. E.; Parsons R. L., Jr.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D.; Luo, C.; Morgan, S. J.; Davis, W. P.; Confalone, P. N.; Chen, C.; Tillyer, R. D.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A. S.; Corley, E. G.; Grabowski, E. J. J.; Reamer, R.; Reider, P. J. J. Org. Chem. 1998, 63, 8536. (b) Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum D. B. J. Am. Chem. Soc. 1998, 120, 2028.
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21. For computational investigations on the origins of enatioselectivities in dialkylzinc additions to benzaldehyde, see (e) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. (f) Goldfuss, B.; Houk, K N. J. Org. Chem. 1998, 63, 8998. (g) Yamakawa, M.; Noyori, R. Organometallics 1999, 18, 128.
22. For computational investigations on the origins of enatioselectivities in dialkylzinc additions to benzaldehyde, see (e) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. (f) Goldfuss, B.; Houk, K N. J. Org. Chem. 1998, 63, 8998. (g) Yamakawa, M.; Noyori, R. Organometallics 1999, 18, 128.
23. For computational investigations on the origins of enatioselectivities in dialkylzinc additions to benzaldehyde, see (e) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. (f) Goldfuss, B.; Houk, K N. J. Org. Chem. 1998, 63, 8998. (g) Yamakawa, M.; Noyori, R. Organometallics 1999, 18, 128.
24. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem. 1995, 107, 1159; Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.
25. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem. 1995, 107, 1159; Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.
26. Williard, P. G.; Sun, C. J. Am. Chem. Soc. 1997, 119, 11693. A similar O-metnyl-α-amino alcohol has been employed by Hogeveen for the enantioselective addition of n-butyllithium to benzaldehyde in 90% ee: Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. For an achiral n-butyllithium trap, see: Brask, J. K.; Chivers, T.; Yap, G. P. A. Chem. Commun. 1998, 2543.
27. Williard, P. G.; Sun, C. J. Am. Chem. Soc. 1997, 119, 11693. A similar O-metnyl-α-amino alcohol has been employed by Hogeveen for the enantioselective addition of n-butyllithium to benzaldehyde in 90% ee: Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. For an achiral n-butyllithium trap, see: Brask, J. K.; Chivers, T.; Yap, G. P. A. Chem. Commun. 1998, 2543.
28. Williard, P. G.; Sun, C. J. Am. Chem. Soc. 1997, 119, 11693. A similar O-metnyl-α-amino alcohol has been employed by Hogeveen for the enantioselective addition of n-butyllithium to benzaldehyde in 90% ee: Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187. For an achiral n-butyllithium trap, see: Brask, J. K.; Chivers, T.; Yap, G. P. A. Chem. Commun. 1998, 2543.
29. (a) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
30. (b) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832.
31. (c) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327.
32. (d) Kitamura, M. Yamakawa, M.; Oka, H.; Suga, S.; Noyori, R. Chem. Eur. J. 1996, 2, 1173.
33. (e) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800.
34. (f) Kitamura, M.; Oka, H.; Noyori, R. Tetrahedron 1999, 55, 3605.
35. Ligand 1 has been synthesized from (-)-fenchone and o-lithioanisole. For the enantiomer of 1, (1S,2S,4R)-2-eredo-hydroxy-2-exo-(o-methoxybenzene)-1,3,3-trimethylbicyclo[2.2. 1]heptane, see: (a) Starling, S. M.; Vonwiller, S. C.; Reek, J. N. H. J. Org. Chem. 1998, 63, 2262. (b) Fry, J. L.; West, J. W. J. Org. Chem. 1981, 46, 2177.
36. Ligand 1 has been synthesized from (-)-fenchone and o-lithioanisole. For the enantiomer of 1, (1S,2S,4R)-2-eredo-hydroxy-2-exo-(o-methoxybenzene)-1,3,3-trimethylbicyclo[2.2. 1]heptane, see: (a) Starling, S. M.; Vonwiller, S. C.; Reek, J. N. H. J. Org. Chem. 1998, 63, 2262. (b) Fry, J. L.; West, J. W. J. Org. Chem. 1981, 46, 2177.
37. all = 0.999. The absolute configuration originates from (-)-fenchone, (1R,4S)-1,3,3-trimethylbieyclo[2.2.1]heptane-2-one.
38. 3 cluster; Cambridge Structural Database (CSD), 1998.
39. trans-C,H distances are 3.14 and 2.52 Å, respectively, and point to the tendency to form "agostic" Li-HC interactions. For short Li-C(H) distances, see: (a) Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. J. Am. Chem. Soc. 1996, 118, 12183. (b) Kottke, T.; Stalke, D. Angew. Chem. 1993, 105, 619; Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
40. trans-C,H distances are 3.14 and 2.52 Å, respectively, and point to the tendency to form "agostic" Li-HC interactions. For short Li-C(H) distances, see: (a) Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. J. Am. Chem. Soc. 1996, 118, 12183. (b) Kottke, T.; Stalke, D. Angew. Chem. 1993, 105, 619; Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
41. trans-C,H distances are 3.14 and 2.52 Å, respectively, and point to the tendency to form "agostic" Li-HC interactions. For short Li-C(H) distances, see: (a) Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. J. Am. Chem. Soc. 1996, 118, 12183. (b) Kottke, T.; Stalke, D. Angew. Chem. 1993, 105, 619; Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
42. 2 the methoxy methyl groups tilt 10.2° out of the aryl plane: Goldfuss, B.; Schleyer, P. v. R.; Handschuh, S.; Hampel, F. J. Organomet. Chem. 1998, 552, 285.
43. all = 1.060. The absolute configuration originates from (-)-fenchone, (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-one.