Application of a Ritter-type reaction to the synthesis of chiral indane-derived C2-symmetric bis(oxazolines)

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 813-814

  Davies, Ian W ^a   Senanayake, Chris H ^a   Larsen, Robert D ^a   Verhoeven, Thomas R ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDAN DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030051486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02328-3     Document Type: Article

References (15)

1. For pioneering work in this area see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726; Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. For related studies see: Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542; Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Letters 1990, 31, 6005.; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232; Nishiyama, H.; Itoh, Y; Matsumoto, H; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
2. For pioneering work in this area see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726; Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. For related studies see: Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542; Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Letters 1990, 31, 6005.; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232; Nishiyama, H.; Itoh, Y; Matsumoto, H; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
3. For pioneering work in this area see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726; Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. For related studies see: Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542; Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Letters 1990, 31, 6005.; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232; Nishiyama, H.; Itoh, Y; Matsumoto, H; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
4. For pioneering work in this area see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726; Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. For related studies see: Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542; Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Letters 1990, 31, 6005.; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232; Nishiyama, H.; Itoh, Y; Matsumoto, H; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
5. For pioneering work in this area see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726; Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. For related studies see: Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542; Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Letters 1990, 31, 6005.; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232; Nishiyama, H.; Itoh, Y; Matsumoto, H; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
6. For pioneering work in this area see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726; Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. For related studies see: Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542; Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Letters 1990, 31, 6005.; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232; Nishiyama, H.; Itoh, Y; Matsumoto, H; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
7. For pioneering work in this area see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726; Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. For related studies see: Bolm, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 542; Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Letters 1990, 31, 6005.; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232; Nishiyama, H.; Itoh, Y; Matsumoto, H; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
8. For leading references see: Denmark, S. E.; Nakajima, N.; Nicaise, O. J.; Faucher, A-M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884.
9. Maligres, P. E.; Upadhyay, V.; Rossen, K.; Ciancosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, R. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Letters 1995, 36, 2195.
10. Senanayake, C. H.; Roberts, F. E.; DiMichele, L. M.; Ryan, K. M.; Liu, J.; Fredenburgh, L. E.; Foster, B. S.; Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Letters 1995, 36, 3993; Senanayake, C. H.; DiMichele, L. M.; Liu, J.; Fredenburgh, L. E.; Ryan, K. M.; Roberts, F. E.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Letters 1995, 36, 7615.
11. Senanayake, C. H.; Roberts, F. E.; DiMichele, L. M.; Ryan, K. M.; Liu, J.; Fredenburgh, L. E.; Foster, B. S.; Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Letters 1995, 36, 3993; Senanayake, C. H.; DiMichele, L. M.; Liu, J.; Fredenburgh, L. E.; Ryan, K. M.; Roberts, F. E.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Letters 1995, 36, 7615.
12. 3) δ 7.52-7.45 (2H, m), 7.30-7.19(6H, m), 5.51(2H, d, J = 9), 5.23(2H, dt, J = 9, 2.5), 3.29(2H, dd, J = 17, 7), 2.93(2H, d, J = 17), 1.42(6H, s). The ligands 4 and 6 were found to be identical in all respects to those prepared independently from 15,2R-1-amino indan-2-ol, thus establishing both the absolute and relative stereochemistry.
13. For related ligands see: Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
14. Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Letters 1995, 56, 7619.
15. Aminoindanol has found related uses: Ghosh, A. K.; Chen, Y. Tetrahedron Letters 1995, 36, 6811.