A new, chiral bis-benzothiazine ligand

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3321-3323

  Harmata, Michael ^a   Ghosh, Sunil K ^a  

^a UNIVERSITY OF MISSOURI   (United States)

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ARTICLE;

EID: 0001314229     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016546n     Document Type: Article

References (14)

1. Handy, S. T. Curr. Org. Chem. 2000, 4, 363-395.
2. Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526.
3. For example, see: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
4. For leading references, see: Reggelin, M.; Zur, C. Synthesis 2000, 1-64.
5. Harmata, M.; Pavri, N. Angew. Chem., Int. Ed. 1999, 38, 2419-21.
6. Bolm, C.; Hildebrand, J. P. Tetrahedron Lett. 1998, 37, 5731-34.
7. Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830-31.
8. The dialdehyde 9 was prepared by oxidation of the corresponding p-xylene, a known compound. See: Gronowitz, S.; Hansen, G. Ark. Kemi 1967, 27, 145-151.
9. 589: +1316.6 (c = 1.05, CHCl3).
10. Brandt, J.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 909-912.
11. For leading references, see: Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8E.
12. 3. Splitting of the signals for one of the two methoxy groups was observed.
13. At room temperature, neither 8 nor 10 was an effective ligand for the allylic alkylation reaction. Little progress was noted in the conversion of 11 to 13 even after 13 days (TLC). The reaction using 8 was also not productive at elevated temperatures in toluene, benzene and dichloromethane.
14. Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.