Concise synthesis of (4S,5S)-4,5-(isopropylidenedioxy)-2-cyclopentenone and a novel C2-symmetric ketone

Tetrahedron Asymmetry

Volumn 8, Issue 10, 1997, Pages 1677-1684

  Armstrong, Alan ^a   Hayter, Barry R ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; HYDROXYLATION; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030965828     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00153-5     Document Type: Article

References (16)

1. For example: McIntosh, J.M.; Cassidy, K.C. Tetrahedron: Asymmetry 1991, 2, 1053-1062. Delucchi, D.; Fabris, F. Synlett 1993, 275-276.
2. For example: McIntosh, J.M.; Cassidy, K.C. Tetrahedron: Asymmetry 1991, 2, 1053-1062. Delucchi, D.; Fabris, F. Synlett 1993, 275-276.
3. Denmark, S.E.; Forbes, D.C.; Hays, D.S.; DePue, J.S.; Wilde, R.G. J. Org. Chem. 1995, 60, 1391-1407.
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5. Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806-9807.
6. It should be noted that there are several elegant literature routes that involve desymmetrisation or resolution of an intermediate or of 1 itself. For example: (a) Johnson, C.R.; Penning, T.D. J. Am. Chem. Soc. 1988, 110, 4726-4735.
7. (b) Johnson, C.R.; Esker, J.L.; Van Zandt, M.C. J. Org. Chem. 1994, 59, 5854-5855.
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9. (d) Deardorff, D.R.; Shambayate, S.; Myles, D.C.; Heerding, D. J. Org. Chem. 1988, 53, 3614-3615.
10. Hill, J.M.; Hutchinson, E.J.; Le Grand, D.M.; Roberts, S.M.; Thorpe, A.J.; Turner, N.J. J. Chem. Soc., Perkin Trans, I, 1994, 1483-1487.
11. Ohrui, H.; Konno, M.; Meguro, H. Agric. Biol. Chem. 1987, 51, 625-626.
12. Hudlicky, T.; Luna, H.; Barbierei, G.; Kwart, L.D. J. Am. Chem. Soc. 1988, 110, 4735-4741.
13. Hudlicky, T.; Natchus, M.G.; Nugent, T.C. Synth. Commun. 1992, 22, 151-157.
14. Stone, K.J.; Little, D.R. J. Org. Chem. 1984, 49, 1849-1853.
15. Wang, Z.-M.; Kakiuchi, K.; Sharpless, K.B. J. Org. Chem. 1994, 59, 6895-6897.
16. For a review of the Sharpless asymmetric dihydroxylation, see: Kolb, H.C.; Van Nieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483-2547.