A new class of modular chiral ligands with fluxional groups

Journal of the American Chemical Society

Volumn 125, Issue 31, 2003, Pages 9306-9307

  Sibi, Mukund P ^a   Zhang, Ruzhou ^a   Manyem, Shankar ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID; ALKADIENE; AMINE; AMINOALCOHOL; COPPER; CYCLOPENTADIENE DERIVATIVE; FLUXIONAL GROUP; FUNCTIONAL GROUP; HYDROXYL GROUP; LEWIS ACID; LIGAND; NAPHTHYL GROUP; NITROGEN; OXIDE; PYRAZOLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; ZINC;

ALKYLATION; ARTICLE; CHIRALITY; CONFORMATION; CYCLOADDITION; DIELS ALDER REACTION; FACE SELECTIVITY; MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKENES; HYDROCARBONS, BROMINATED; LIGANDS; MODELS, MOLECULAR; PYRAZOLES; STEREOISOMERISM;

EID: 0042201920     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035979d     Document Type: Article

References (20)

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7. For the use of meso and achiral ligands in asymmetric synthesis, (a) see: Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802. (b) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929. (c) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161. (d) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Matsukawa, S. Acc. Chem. Res. 2000, 33, 391. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478. (f) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Guindet, P.; Vallée, Y. Tetrahedron: Asymmetry 1998, 9, 3889. (g) Mikami, K.; Aikawa, K.; Ysa, Y.; Jordy, J. J.; Yamanaka, M. Synlett 2002, 1561.
8. For the use of meso and achiral ligands in asymmetric synthesis, (a) see: Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802. (b) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929. (c) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161. (d) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Matsukawa, S. Acc. Chem. Res. 2000, 33, 391. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478. (f) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Guindet, P.; Vallée, Y. Tetrahedron: Asymmetry 1998, 9, 3889. (g) Mikami, K.; Aikawa, K.; Ysa, Y.; Jordy, J. J.; Yamanaka, M. Synlett 2002, 1561.
9. For the use of meso and achiral ligands in asymmetric synthesis, (a) see: Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802. (b) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929. (c) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161. (d) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Matsukawa, S. Acc. Chem. Res. 2000, 33, 391. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478. (f) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Guindet, P.; Vallée, Y. Tetrahedron: Asymmetry 1998, 9, 3889. (g) Mikami, K.; Aikawa, K.; Ysa, Y.; Jordy, J. J.; Yamanaka, M. Synlett 2002, 1561.
10. For the use of meso and achiral ligands in asymmetric synthesis, (a) see: Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802. (b) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929. (c) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161. (d) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Matsukawa, S. Acc. Chem. Res. 2000, 33, 391. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478. (f) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Guindet, P.; Vallée, Y. Tetrahedron: Asymmetry 1998, 9, 3889. (g) Mikami, K.; Aikawa, K.; Ysa, Y.; Jordy, J. J.; Yamanaka, M. Synlett 2002, 1561.
11. For the use of meso and achiral ligands in asymmetric synthesis, (a) see: Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802. (b) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929. (c) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161. (d) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Matsukawa, S. Acc. Chem. Res. 2000, 33, 391. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478. (f) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Guindet, P.; Vallée, Y. Tetrahedron: Asymmetry 1998, 9, 3889. (g) Mikami, K.; Aikawa, K.; Ysa, Y.; Jordy, J. J.; Yamanaka, M. Synlett 2002, 1561.
12. For the use of meso and achiral ligands in asymmetric synthesis, (a) see: Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802. (b) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929. (c) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161. (d) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Matsukawa, S. Acc. Chem. Res. 2000, 33, 391. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478. (f) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Guindet, P.; Vallée, Y. Tetrahedron: Asymmetry 1998, 9, 3889. (g) Mikami, K.; Aikawa, K.; Ysa, Y.; Jordy, J. J.; Yamanaka, M. Synlett 2002, 1561.
13. Achiral templates with fluxional groups in synthesis, see: (a) Sibi, M. P.; Venkatraman, L.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 2001, 123, 8444. (b) Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chem.-Eur. J. 2003, 9, 28. (c) Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181.
14. Achiral templates with fluxional groups in synthesis, see: (a) Sibi, M. P.; Venkatraman, L.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 2001, 123, 8444. (b) Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chem.-Eur. J. 2003, 9, 28. (c) Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181.
15. Achiral templates with fluxional groups in synthesis, see: (a) Sibi, M. P.; Venkatraman, L.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 2001, 123, 8444. (b) Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chem.-Eur. J. 2003, 9, 28. (c) Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181.
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18. For the synthesis of ligands, reaction conditions for DA reactions, ee determination, and product stereochemical analysis, see the Supporting Information.
19. 2 as a Lewis acid, see: (a) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., II. Tetrahedron: Asymmetry 1997, 8, 3079. (b) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.
20. 2 as a Lewis acid, see: (a) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., II. Tetrahedron: Asymmetry 1997, 8, 3079. (b) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.