Chiral, bicyclic proline derivatives and their application as ligands for copper in the catalytic asymmetric allylic oxidation of olefins

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7577-7580

  Södergren, Mikael J ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CYCLOALKENE; PROLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030583506     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01664-4     Document Type: Article

References (16)

1. 1) Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1959, 81, 5819.
2. 2) Levina, A.; Muzart, J. Tetrahedron: Asymmetry 1995, 6, 147; Synth. Commun. 1995, 25, 1789.
3. Levina, A.; Muzart, J. Tetrahedron: Asymmetry 1995, 6, 147; Synth. Commun. 1995, 25, 1789.
4. 3) Rispens, M. T.; Zondervan, C.; Feringa, B. L. Tetrahedron: Asymmetry, 1995, 6, 661.
5. 4) Stella, L.; Abraham, H. Tetrahedron Lett. 1990, 31, 2603.
6. 5) Bishop, J. E.; O'Conell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. The product obtained is a mixture of benzyl glyoxylate and its trimer, of which both components are active in the following condensation reaction.
7. 3N 97:2:1) afforded (in order of elution) minor exo-isomer (35 mg), major endo-isomer (not characterized) and major exo-isomer (1.23 g, 83%) as colorless oils.
8. +, 3), 198 (48), 106 (18), 105 (100), 103 (11), 79 (17), 77 (20).
9. +, 5), 213 (15), 212 (100), 184 (43), 105 (83), 91 (44), 80 (71), 79 (24), 77 (17).
10. 9) Given values represent selected observed NOE enhancements. Absolute configuration assignments are based on comparisons with earlier reported ciroptical data (refs. 2,4).
11. 2 (5 atm) for 24 hours. Filtration through a pad of celite and concentration yielded 7 as white crystals (423 mg, 100%).
12. +, 3), 96 (50), 80(4), 68 (100), 56 (29).
13. +, 5), 122 (12), 111 (18), 110 (95), 109 (19), 82 (100), 80 (33).
14. 13) During the course of this study, the use of bis-oxazoline-type ligands has also been reported, see for example a) Andrus, M.B.; Argade, A.B.; Chen, X.; Pamment, M.G. Tetrahedron Lett. 1995, 36, 2945; b) Gokale, A. S.; Mindis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831; c) Gupta, A. D.; Singh, V. K. Tetrahedron Lett. 1996, 37, 2633.
15. During the course of this study, the use of bis-oxazoline-type ligands has also been reported, see for example a) Andrus, M.B.; Argade, A.B.; Chen, X.; Pamment, M.G. Tetrahedron Lett. 1995, 36, 2945; b) Gokale, A. S.; Mindis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831; c) Gupta, A. D.; Singh, V. K. Tetrahedron Lett. 1996, 37, 2633.
16. During the course of this study, the use of bis-oxazoline-type ligands has also been reported, see for example a) Andrus, M.B.; Argade, A.B.; Chen, X.; Pamment, M.G. Tetrahedron Lett. 1995, 36, 2945; b) Gokale, A. S.; Mindis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831; c) Gupta, A. D.; Singh, V. K. Tetrahedron Lett. 1996, 37, 2633.