The critical importance of water in the asymmetric allylboration of N- trimethylsilylbenzaldimines with B-allyldiisopinocampheylborane

Angewandte Chemie - International Edition

Volumn 38, Issue 6, 1999, Pages 825-826

  Chen, Guang Ming ^a   Ramachandran, P Veeraraghavan ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Aldehydes; Asymmetric synthesis; Boranes; Homoallylamines; Imines

Indexed keywords

ALDEHYDE; ALLYLAMINE DERIVATIVE; BORANE DERIVATIVE; IMINE; WATER;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0033559915     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990315)38:6<825::AID-ANIE825>3.0.CO;2-V     Document Type: Article

References (18)

1. a) H. C. Brown, P. V. Ramachandran, Advances in Asymmetric Synthesis, Vol. I (Ed.: A. Hassner) JAI, Greenwich, CT, 1995, chap. 5;
2. b) H. C. Brown, P. V. Ramachandran, J. Organomet. Chem. 1995, 500, 1-19.
3. H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092.
4. Examples of such applications: a) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059; b) A. B. Smith, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1995, 117, 12013-12014; c) K. C Nicolaou, M. E. Bunnage, K. Koide, J. Am. Chem. Soc. 1994, 116, 8402-8403.
5. Examples of such applications: a) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059; b) A. B. Smith, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1995, 117, 12013-12014; c) K. C Nicolaou, M. E. Bunnage, K. Koide, J. Am. Chem. Soc. 1994, 116, 8402-8403.
6. Examples of such applications: a) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059; b) A. B. Smith, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1995, 117, 12013-12014; c) K. C Nicolaou, M. E. Bunnage, K. Koide, J. Am. Chem. Soc. 1994, 116, 8402-8403.
7. P. V. Ramachandran, G.-M. Chen, H. C. Brown, Tetrahedron Lett. 1997, 38, 2417-2420.
8. a) Y. Yamamoto, W. Ito, K. Maruyama, J. Chem. Soc. Chem. Commun. 1985, 1131-1132;
9. b). Y. Yamamoto, T. Koshiaki, K. Maruyama, J. Org. Chem. 1985, 50, 3115-3121;
10. c) Y. Yamamoto, S. Nishi, K. Maruyama, T. Komatsu, W. Ito, J. Am. Chem. Soc. 1986, 108, 7778-7786.
11. a) K. Watanabe, K. Ito, S. Itsuno, Tetrahedron: Asymmetry 1995, 6, 1531-1534;
12. b) S. Itsuno, K. Watanabe, K. Ito, A. A. El-Shehawy, A. A. Sarhan, Angew. Chem. 1997 109, 105-107: Angew. Chem. Int. Ed. Engl. 1997, 36, 109-110.
13. b) S. Itsuno, K. Watanabe, K. Ito, A. A. El-Shehawy, A. A. Sarhan, Angew. Chem. 1997 109, 105-107: Angew. Chem. Int. Ed. Engl. 1997, 36, 109-110.
14. I. Chataigner, F. Zammattio, J. Lebreton, J. Villieras, Synlett 1998, 275-276.
15. H. C. Brown, U. S. Racherla, P. J. Pellechia, J. Org. Chem. 1990, 55, 1868-1874.
16. D. J. Hart, K. Kanai, D. G. Thomas, T.-K. Yang, J. Org. Chem. 1983, 48, 289-294.
17. a) T. Basile, A. Bocoum, D. Savoia, A. Umani-Ronchi, J. Org. Chem. 1994, 59, 7766-7773;
18. b) S. Liu, A. Mi, L. Wu, Y. Jiang, Synth. Commun. 1993, 23, 2485-2488.