Diastereospecific epoxidation/AE kinetic resolution of cis/trans-2,6-dimethylbenzylidene cyclohexane and solution conformation of 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8447-8450

  Gardiner, John M ^a   Nørret, Marck ^a   Sadler, Ian H ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 16044375009     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01915-6     Document Type: Article

References (21)

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2. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; VCH, New York, 1993; Chapter 4.1.
3. rel=2.7-9.3 (2.7, 3.1, 3.4, 3.9, 4.5, 5.4, 6.1, 6.9, 9.3)
4. 3. Gardiner, J. M.; Nørret, M. N.; Sadler, I. H. submitted for publication.
5. 4. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
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10. 8. VanNieuwenhze, M. S.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7864.
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13. 11. 40% conversion using catalytic AD conditions took ≥8 hrs. Furthermore, using an achiral version of the same dihydroxylation conditions was much slower than AD.
14. 12. Chiralpak cyclodextrin-β chiral g.c. column. Retention times: (±)-1 13.1min; ent-2 13.4 min; 2 13.6 min.
15. + 217.
16. rel = ln[1-C)(1-e.e.)]/[ln[(1-C)(1+e.e.)], where C=conversion. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
17. 15. Alphabetic labels refer to observed signals from lowest frequency (A) to highest frequency (L).
18. 16. Full details and discussion of the NMR-based conformational analyses will be reported elsewhere.
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20. 18. (a) Epoxidation and other electrophilic additions of 2-methylexomethylene cyclohexane: Bellucci, G.; Chiappe, C.; Lo Moro, G.; Ingrosso, G. J. Org. Chem. 1995, 60, 6214.
21. (b) A study of stereoelectronic contributions in a series of substrates: Vedejs, E.; Dent, W. H. III J. Am. Chem. Soc. 1989, 111, 6861.