Synthesis and resolution of a novel chiral diamine ligand and application to asymmetric lithiation-substitution

Organic Letters

Volumn 2, Issue 7, 2000, Pages 875-878

  Li, Xiaolin ^a   Schenkel, Laurie B ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001176845     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9903133     Document Type: Article

References (21)

1. (a) Lucet, D.; LeGall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627.
2. (b) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3195.
3. (c) Mukaiyama, T.; Asami, M. Top. Curr. Chem. 1985, 127, 133-167.
4. (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.
5. (b) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
6. Kozlowski, M. C.; Evans, C. A. Submitted for publication.
7. Armarego, W. L. F. J. Chem. Soc. C 1967, 377-383.
8. 2: Albert, A. J. Chem. Soc. 1960, 1790-3.
9. Hoffmann et al. have independently shown that similar reaction conditions result in similar improvement (see ref 12a).
10. 2O afforded a 94:6 mixture of cis-10 and the trans isomer. Distillation (89-90 °C, 3 mmHg) afforded pure 10 (4.2 g, 48%) as a waxy white solid. See Supporting Information for analytical data.
11. 2O caused enrichment to ≥ 98% ee (458 mg, 83%). See Supporting Information for analytical data.
12. 2:MeOH) to afford 11e (0.98 g, 93%) as a waxy white solid. See Supporting Information for analytical data.
13. (a) Park, Y. S.; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 10537-8.
14. (b) Curtis, M. D.; Beak, P. J. Org. Chem. 1999, 64, 2296-7.
15. (a) Gallagher, D. J.; Wu, S.; Nikolic, N. A.; Beak, P. J. Org. Chem. 1995, 60, 8148-54.
16. (b) Uemura, M.; Hayashi, Y.; Hayashi, Y. Tetrahedron: Asymmetry 1994, 5, 1427-30.
17. (c) Hoffmann, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. 2 1995, 1721-6.
18. (a) Santos, A. G.; Klute, W.; Torode, J.; Böhm, V. P. W.; Carbrita, E.; Runsink, J.; Hoffmann, R. W. New. J. Chem. 1998, 993-7.
19. (b) Fleischhauer, J.; Raabe, G.; Santos, A. G.; Schiffer, J.; Wollmer, A. Z. Naturforsch. A: Phys. Sci. 1998, 53, 896-902.
20. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231-9,
21. Thayumanavan, S.; Basu, A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 8209-16.