Solvent induced isomerization of 2-cyclohexen-1-ol to 3-cyclohexen-1-ol by a chiral lithium amide

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 399-402

  Khan, Agha Zul Qarnian ^a   Arvidsson, Per I ^a   Ahlberg, Per ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

3 CYCLOHEXENOL; CYCLOHEXANOL DERIVATIVE; CYCLOHEXENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; PRIORITY JOURNAL;

EID: 0001640083     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00017-1     Document Type: Article

References (27)

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19. Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc., 1994, 116, 6009-6010 and references cited therein.
20. Chiral columns with stationary phases octakis (6-O -methyl-2,3-di-O-pentyl)-α-cyclodextrin and heptakis-(2,6-di-O-methyl-3-O-pentyl)-β-cyclodextrin supplied by König (König, W. A.; Guhrcke, B.; Icheln, D.; Evers, P; Dönnecke, J.; Wang, W., J. High Resolut. Chromatogr. 1992, 15, 367-372).
21. (a) To an ice-cold solution of diamine precursor of 1 (0.61 mmol) in 2 ml of 2,5-DMTHF, 0.61 mmol of n-BuLi (1.7 M in hexane) was added and kept at 0°C for 30 minutes. Cyclohexene oxide (0.51 mmol) was added and reaction mixture was allowed to reach ambient temperature. At intervals, 10 μl of the sample was withdrawn and the reaction was quenched with 100 μl of ammonium chloride solution, neutralized with 0.5 M HCl, washed with brine and water, dried over anhydrous sodium sulphate and injected (1 μl) on the GC column;
22. (b) Cyclohexene oxide and (±)-2-cyclohexen-1-ol were commercially available;
23. We thank Professor König for a gift of a mixture of (±)-2-cyclohexen-1-ol and (±)-3-cyclohexen-1-ol. It was also prepared according to Crandall, J. K.; Chang, L-Ho. J. Org. Chem., 1967, 32, 435-439;
24. 3a-c, 3f 10. A Fischer SPALTROHR distillation column was used to separate the 2,5-DMTHF (52% cis and 48% trans mixture) into corresponding 99% cis and 98% trans-isomers and analysed by GC.
25. Reactions were performed as mentioned in 9 (a). Instead of cyclohexene oxide, 0.21 mmol of (±)-2-cyclohexen-1-ol was added. Workup as usual. The reactions were followed by GC up to 48 hours.
26. (a) Kissel, C. L.; Rickborn, B. J. Org. Chem., 1972, 37, 2060-2063;
27. (b) Thummel, R. P.; Rickborn, B. J. Org. Chem., 1972, 37, 3919-3923.