An asymmetric phase-transfer dihydroxylation reaction

Angewandte Chemie - International Edition

Volumn 41, Issue 18, 2002, Pages 3479-3480

  Bhunnoo, Riaz A ^a   Hu, Yulai ^a   Lainé, Dramane I ^b   Brown, Richard C D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Asymmetric synthesis; Dihydroxylation; Diols; Oxidation; Phase transfer catalysis

Indexed keywords

HYDROXYLATION; PHASE TRANSITIONS;

DIHYDROXYLATION;

ORGANIC COMPOUNDS;

ALKENE; OSMIUM; PERMANGANATE POTASSIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DIHYDROXYLATION; ENANTIOMER; OXIDATION; PHASE TRANSITION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037119780     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20020916)41:18<3479::AID-ANIE3479>3.0.CO;2-O     Document Type: Article

References (23)

1. For a selection of recent reviews on asymmetric dihydroxylation see: a) H. Waldmann in Organic Synthesis Highlights II, (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 9-18; b) H. C. Kolb, M. S. Vannieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis 2nd ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 357-398; d) C. Bolm, J. P. Hildebrand, K. Muñiz in Catalytic Asymmetric Synthesis, 2nd ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 399-428.
2. For a selection of recent reviews on asymmetric dihydroxylation see: a) H. Waldmann in Organic Synthesis Highlights II, (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 9-18; b) H. C. Kolb, M. S. Vannieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis 2nd ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 357-398; d) C. Bolm, J. P. Hildebrand, K. Muñiz in Catalytic Asymmetric Synthesis, 2nd ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 399-428.
3. For a selection of recent reviews on asymmetric dihydroxylation see: a) H. Waldmann in Organic Synthesis Highlights II, (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 9-18; b) H. C. Kolb, M. S. Vannieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis 2nd Ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 357-398; d) C. Bolm, J. P. Hildebrand, K. Muñiz in Catalytic Asymmetric Synthesis, 2nd ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 399-428.
4. For a selection of recent reviews on asymmetric dihydroxylation see: a) H. Waldmann in Organic Synthesis Highlights II, (Ed.: H. Waldmann), VCH, Weinheim, 1995, pp. 9-18; b) H. C. Kolb, M. S. Vannieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis 2nd Ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 357-398; d) C. Bolm, J. P. Hildebrand, K. Muñiz in Catalytic Asymmetric Synthesis, 2nd Ed., (Ed.: I. Ojima), Wiley-VCH, New York 2000, pp. 399-428.
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10. 4 see: A. W. M. Lee, W. H. Chan, W. H. Yuen, P. F. Xia, W. Y. Wong, Tetrahedron: Asymmetry 1999, 10, 1421-1424.
11. For an earlier example of asymmetric oxidation using permanganate in the presence of a chiral quaternary ammonium salt see: R. C. D. Brown, J. F. Keily, Angew. Chem. 2001, 113, 4628-4630; Angew. Chem. Int. Ed. 2001, 40, 4496-4498.
12. For an earlier example of asymmetric oxidation using permanganate in the presence of a chiral quaternary ammonium salt see: R. C. D. Brown, J. F. Keily, Angew. Chem. 2001, 113, 4628-4630; Angew. Chem. Int. Ed. 2001, 40, 4496-4498.
13. For examples of the nucleophilic epoxidation reactions of enones using asymmetric phase-transfer catalysis see: a) J. C. Hummelen, H. Wynberg, Tetrahedron Lett. 1978, 1089-1092; b) R. Helder, J. C. Hummelen, J. S. Laane, J. S. Weiring, H. Wynberg, Tetrahedron Lett. 1976, 1831-1834; c) B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599-1602; d) B. Lygo, P. G. Wainwright, Tetrahedron 1999, 55, 6289-6300; e) B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343-1346; f) E. J. Corey, F. Y. Zhang, Org. Lett. 1999, 1, 1287-1290.
14. For examples of the nucleophilic epoxidation reactions of enones using asymmetric phase-transfer catalysis see: a) J. C. Hummelen, H. Wynberg, Tetrahedron Lett. 1978, 1089-1092; b) R. Helder, J. C. Hummelen, J. S. Laane, J. S. Weiring, H. Wynberg, Tetrahedron Lett. 1976, 1831-1834; c) B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599-1602; d) B. Lygo, P. G. Wainwright, Tetrahedron 1999, 55, 6289-6300; e) B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343-1346; f) E. J. Corey, F. Y. Zhang, Org. Lett. 1999, 1, 1287-1290.
15. For examples of the nucleophilic epoxidation reactions of enones using asymmetric phase-transfer catalysis see: a) J. C. Hummelen, H. Wynberg, Tetrahedron Lett. 1978, 1089-1092; b) R. Helder, J. C. Hummelen, J. S. Laane, J. S. Weiring, H. Wynberg, Tetrahedron Lett. 1976, 1831-1834; c) B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599-1602; d) B. Lygo, P. G. Wainwright, Tetrahedron 1999, 55, 6289-6300; e) B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343-1346; f) E. J. Corey, F. Y. Zhang, Org. Lett. 1999, 1, 1287-1290.
16. For examples of the nucleophilic epoxidation reactions of enones using asymmetric phase-transfer catalysis see: a) J. C. Hummelen, H. Wynberg, Tetrahedron Lett. 1978, 1089-1092; b) R. Helder, J. C. Hummelen, J. S. Laane, J. S. Weiring, H. Wynberg, Tetrahedron Lett. 1976, 1831-1834; c) B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599-1602; d) B. Lygo, P. G. Wainwright, Tetrahedron 1999, 55, 6289-6300; e) B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343-1346; f) E. J. Corey, F. Y. Zhang, Org. Lett. 1999, 1, 1287-1290.
17. For examples of the nucleophilic epoxidation reactions of enones using asymmetric phase-transfer catalysis see: a) J. C. Hummelen, H. Wynberg, Tetrahedron Lett. 1978, 1089-1092; b) R. Helder, J. C. Hummelen, J. S. Laane, J. S. Weiring, H. Wynberg, Tetrahedron Lett. 1976, 1831-1834; c) B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599-1602; d) B. Lygo, P. G. Wainwright, Tetrahedron 1999, 55, 6289-6300; e) B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343-1346; f) E. J. Corey, F. Y. Zhang, Org. Lett. 1999, 1, 1287-1290.
18. For examples of the nucleophilic epoxidation reactions of enones using asymmetric phase-transfer catalysis see: a) J. C. Hummelen, H. Wynberg, Tetrahedron Lett. 1978, 1089-1092; b) R. Helder, J. C. Hummelen, J. S. Laane, J. S. Weiring, H. Wynberg, Tetrahedron Lett. 1976, 1831-1834; c) B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599-1602; d) B. Lygo, P. G. Wainwright, Tetrahedron 1999, 55, 6289-6300; e) B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343-1346; f) E. J. Corey, F. Y. Zhang, Org. Lett. 1999, 1, 1287-1290.
19. D. G. Lee in Oxidation in Organic Chemistry, Part D, (Ed.: W. S. Trahanovsky), Academic Press, San Diego, 1982, pp. 147-206.
20. Enones 4a-h were prepared according to the following procedure: W. S. Wadsworth, Jr., W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 1733-1738.
21. X-ray structural determination: Y. Li, M. B. Hursthouse, personal communication.
22. t = 10.22 min (major). Absolute stereochemistry of 1,2-dihydroxy-1-phenylethane was determined by optical rotation, which gave 20% ee by comparison to a sample from Aldrich.
23. Method for preparation of cyclic carbonates: K. Matsumotu, Y. Sato, M. Shimojo, M. Hatanaka, Tetrahedron: Asymmetry 2000, 11, 1965-1973.