Diastereoselective and enantioselective substitution reactions of an isoindoline-borane complex

Synlett

Volumn , Issue 2, 1998, Pages 189-191

  Blake, Alexander J ^a   Ebden, Mark R ^a   Fox, David N A ^b   Li, Wan Sheung ^a   Simpkins, Nigel S ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002377194     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1611     Document Type: Article

References (20)

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2. See also (b) Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327.
3. For a review, see (c) Kessar, S. V.; Singh, P. Chem. Rev. 1997, 97, 721.
4. Ebden, M. R.; Simpkins, N. S.; Fox, D. N. A. Tetrahedron Lett. 1995, 36, 8697.
5. (a) Ferey, V.; Le Gall, T.; Mioskowski, C. J. Chem. Soc., Chem. Commun. 1995, 487.
6. (b) Ferey, V.; Vedrenne, P.; Toupet, L.; LeGall, T.; Mioskowski, C. J. Org. Chem. 1996, 61, 7244.
7. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941.
8. For previous asymmetric aproaches, see (a) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381.
9. (b) Meyers, A. I.; Santiago, B. Tetrahedron Lett. 1995, 36, 5877.
10. For possible pharmacological applications, see (a) Young, P.; Berge, J.; Chapman, H.; Cawthorne, M. A. Eur. J. Pharmacol. 1989, 168, 381.
11. (b) Cignarella, G.; Sanna, P.; Miele, E.; Anania, V.; Desole, M. S. J. Med. Chem. 1981, 24, 1003.
12. 3, judging from the B-H bond length (1.13(2) Å) compared to the C-H (0.96 Å, idealised).
13. At present we assume that the major stereoisomer is 8 in all cases; confirmation of this assignment for electrophiles other than MeI is being sought.
14. (a) Lithiated N-formamidine tetrahydroisoquinoline derivatives are similarly configurationally unstable, see Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505.
15. See also (b) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
16. (c) Elworthy, T. R.; Meyers, A. I. Tetrahedron 1994, 50, 6089.
17. 22BNSi requires (M-H), 218.1536).
18. 3) to give samples of identical free amine product having the same sense of specific rotation.
19. 3SiCl could influence aspects of the remainder of the quench (rate, stereoselectivity, etc.). See Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry VCH, New York, 1991.
20. Wittig, G.; Streib, H. Liebigs Ann. Chem. 1953, 584, 1. Our sample of ammonium iodide had m.p. 150-2 °C; the cited work quotes a m.p. of 145.5-147 °C for the racemic material.