New, improved procedure for the synthesis of structurally diverse N-spiro C2-symmetric chiral quaternary ammonium bromides

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4576-4578

  Ooi, Takashi ^a   Uematsu, Yukitaka ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILES;

AMMONIUM COMPOUNDS; BROMINE COMPOUNDS; MAGNESIUM COMPOUNDS; MOLECULAR STRUCTURE; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

2,2' BIS(ISOPROPOXYCARBONYL) 1,1' BINAPHTHYL; AMMONIUM BROMIDE; AMMONIUM DERIVATIVE; BROMINE; CARBONYL DERIVATIVE; IODINE; MAGNESIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PHASE TRANSITION; REACTION ANALYSIS; REACTION OPTIMIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038779271     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030032f     Document Type: Article

References (15)

1. (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519.
2. (b) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339.
3. (c) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551.
4. (d) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
5. (e) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
6. (a) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228.
7. (b) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716.
8. For review, see: Suzuki, A. J. Organomet. Chem. 1999, 576, 147 and references therein.
9. (a) Eaton, P. E.; Lee, C.-H.; Xiiong, Y. J. Am. Chem. Soc. 1989, 111, 8016.
10. (b) Henderson, K. W.; Kerr, W. J. Chem. Eur. J. 2001, 7, 3430.
11. 2 in the reaction with 6 gave totally unsatisfactory results. For instance, treatment of 6 with 2.2 equiv of LiTMP in THF at 0 °C for 2 h and subsequent reaction with bromine (2.2 equiv) at -78 °C to room temperature resulted in almost total recovery of starting 6, while both attempts to use 3 equiv of LiTMP and to perform the lithiation at room temperature gave a deteriorated mixture.
12. (a) Ohta, T.; Ito, M.; Inagaki, K.; Takaya, H. Tetrahedron Lett. 1993, 34, 1615.
13. (b) Seki, M.; Yamada, S.; Kuroda, T.; Imashiro, R.; Shimizu, T. Synthesis 2000, 1677.
14. 1H NMR).
15. Concomitant formation of monobromination product was observed (ca. 25%). Magnesiation of 6 under more concentrated condition (0.62 M) or at higher temperature (50 °C) did not lead to the improvement of the chemical yield of 5a, as long as 3 equiv of Mg(TMP)2 was used.