B-Methoxydiisopinocampheylborane (Ipc2BOMe): A Pinene Based Auxiliary for Asymmetric C-C Bond-Forming Reactions

Advanced Synthesis and Catalysis

Volumn 341, Issue 1, 1999, Pages 83-87

  Hertweck, Christian ^a   Boland, Wilhelm ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

Allylation agents; Asymmetric synthesis; Boron; C C coupling; Chiral auxiliaries; Reagents

Indexed keywords

EID: 0346524699     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3897(199901)341:1<83::aid-prac83>3.0.co;2-1     Document Type: Article

References (39)

1. A. Hassner (Ed.), Advances in Asymmetric Synthesis, Vol. 1, JAI Press, Greenwich, CT, 1995
2. G. J. McGarvey (Ed.), Advances in Asymmetric Induction, JAI Press, Greenwich, CT, 1995
3. H. C. Brown, P. V. Ramachandran, J. Organomet. Chem. 1995, 500, 1
4. H. C. Brown, U. S. Racherla, Y. Liao, V. V. Khanna, J. Org. Chem. 1992, 57, 6608
5. U.S. Racherla, H.C. Brown, J. Org. Chem. 1991, 56, 401. (and references cited herein)
6. R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 1982, 21, 555; W. R. Roush, Allyl Organometallics, in: Comprehensive Organic Synthesis, Vol. 2, (B. M. Trost, I. Fleming and C. H. Heathcock, Eds.), Pergamon Press, Oxford 1991, 1
7. R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 1982, 21, 555; W. R. Roush, Allyl Organometallics, in: Comprehensive Organic Synthesis, Vol. 2, (B. M. Trost, I. Fleming and C. H. Heathcock, Eds.), Pergamon Press, Oxford 1991, 1
8. H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092; H. C. Brown, K. S. Bhat, R. S. Randad, J. Org. Chem. 1987, 52, 320
9. H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092; H. C. Brown, K. S. Bhat, R. S. Randad, J. Org. Chem. 1987, 52, 320
10. R. D. Groneberg, T. Miyazaki, N. A. Stylianides, T. J. Schulze, W. Stahl, E. P. Schreiner, T. Suzuki, Y. Iwabucchi, A. L. Smith, K. C. Nicolaou, J. Am. Chem. Soc. 1993, 115, 7593
11. K. Faber, in: Biotransformations in Organic Chemistry, Springer Verlag, Heidelberg 1997, and ref. cited therein; C. Hertweck, W. Boland, J. Prakt. Chem. 1997, 339, 200; C. Hertweck, W. Boland, J. Prakt. Chem. 1997, 339, 754
12. K. Faber, in: Biotransformations in Organic Chemistry, Springer Verlag, Heidelberg 1997, and ref. cited therein; C. Hertweck, W. Boland, J. Prakt. Chem. 1997, 339, 200; C. Hertweck, W. Boland, J. Prakt. Chem. 1997, 339, 754
13. K. Faber, in: Biotransformations in Organic Chemistry, Springer Verlag, Heidelberg 1997, and ref. cited therein; C. Hertweck, W. Boland, J. Prakt. Chem. 1997, 339, 200; C. Hertweck, W. Boland, J. Prakt. Chem. 1997, 339, 754
14. Z. Wang, D. Deschenes, J. Am. Chem. Soc. 1992, 114, 1090
15. Y. Mori, Y. Kohchi, M. Suzuki, J. Org. Chem. 1991, 56, 631, and ref. cited therein
16. H. C. Brown, R. S. Randad, Tetrahedron 1990, 46, 4463; H. C. Brown, R. S. Randad, Tetrahedron Lett. 1990, 31, 455
17. H. C. Brown, R. S. Randad, Tetrahedron 1990, 46, 4463; H. C. Brown, R. S. Randad, Tetrahedron Lett. 1990, 31, 455
18. H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 293; H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 5919
19. H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 293; H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 5919
20. A. G. M. Barrett, S. Lebold, J. Org. Chem. 1991, 56, 4875
21. K. C. Nicolaou, P. Bertinato, A. D. Piscopio, T. K. Chakraborty, N. Minowa, J. Chem. Soc., Chem. Commun. 1993, 619
22. K. Burgess, I. Henderson, Tetrahedron Lett. 1990, 31, 6949
23. H. C. Brown, P. K. Jadhav, K. S. Bhat, J. Am. Chem. Soc. 1988, 110, 1535
24. A. G. M. Barrett, J. W. Malecha, J. Chem. Soc., Perkin Trans. 1 1994, 14, 1901
25. A. L. Smith, E. N. Pitsinos, C.-K. Hwang, Y. Mizuno, H. Saimoto, G. R. Scarlato, T. Suzuki, K. C. Nicolaou, J. Am. Chem. Soc. 1993, 115, 7612
26. M. Nakata, T. Osumi, A. Ueno, T. Kimura, T. Tamai, K. Tatsuka, Tetrahedron Lett. 1991, 32, 6015; M. Nakata, T. Osumi, A. Ueno, T. Kimura, T. Tamai, K. Tatsuka, Bull. Chem. Soc. Jpn. 1992, 65, 2974
27. M. Nakata, T. Osumi, A. Ueno, T. Kimura, T. Tamai, K. Tatsuka, Tetrahedron Lett. 1991, 32, 6015; M. Nakata, T. Osumi, A. Ueno, T. Kimura, T. Tamai, K. Tatsuka, Bull. Chem. Soc. Jpn. 1992, 65, 2974
28. K. Burgess, D. A. Chaplin, I. Henderson, Y. T. Pan, A. D. Elbein, J. Org. Chem. 1992, 57, 1103
29. A. G. M. Barrett, J. W. Malecha, J. Org. Chem. 1991, 56, 5243
30. A. G. M. Barrett, M. A. Seefeld, Tetrahedron 1993, 49, 7857
31. A. G. M. Barrett, M. A. Seefeld, J. Chem. Soc., Chem. Commun. 1993, 339
32. A. G. M. Barrett, M. A. Seefeld, D. J. William, J. Chem. Soc., Chem. Commun. 1994, 1053; A. G. M. Barrett, M. A. Seefeld, A. J. P. White, D. J. Williams, J. Org. Chem. 1996, 61, 2677
33. A. G. M. Barrett, M. A. Seefeld, D. J. William, J. Chem. Soc., Chem. Commun. 1994, 1053; A. G. M. Barrett, M. A. Seefeld, A. J. P. White, D. J. Williams, J. Org. Chem. 1996, 61, 2677
34. C. Hertweck, W. Boland, in: "Recent Developments in Synthetic Organic Chemistry. (S. G. Pandalai, Ed.) Transworld Research Network 1999 in press.
35. S. Jayaraman, S. Hu, A. C. Oehlschlager, Tetrahedron Lett. 1995, 36, 4765
36. S. Hu, S. Jayaraman, A. C. Oehlschlager, J. Org. Chem. 1996, 61, 7513
37. C. Hertweck, H. Goerls, W. Boland, J. Chem. Soc., Chem. Commun. 1988, 18, 1955
38. C. Hertweck, W. Boland, Eur. J. Org. Chem. 1998, 2143
39. C. Hertweck, W. Boland, Tetrahedron 1997, 53, 14651