Unexpected stereoselectivity in the cis dihydroxylation of some 2- cyclopentene-1-carboxamides

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4601-4604

  Palmer, Christopher F ^a   McCague, Raymond ^a   Ruecroft, Graham ^a   Savage, Sean ^a   Taylor, Stephen J C ^a   Ries, Christel ^a  

^a Chiroscience Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMIDE; CYCLOPENTANE DERIVATIVE; NUCLEOSIDE;

ARTICLE; CIS ISOMER; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; MASS SPECTROMETRY; STEREOISOMERISM; VASODILATATION;

EID: 0030600191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00887-8     Document Type: Article

References (12)

1. 1. Marquez V.E.; Lim M.I., Med. Res. Rev., 1986, 6, 1; Borthwick A.D.; Biggadike K., Tetrahedron, 1992, 48,571.
2. 1. Marquez V.E.; Lim M.I., Med. Res. Rev., 1986, 6, 1; Borthwick A.D.; Biggadike K., Tetrahedron, 1992, 48,571.
3. 2. Chen J.; Grim M., Rock C.; Chan K., Tetrahedron Lett. 1989, 30, 5543.
4. 3. Taylor S.J.C.; McCague R.; Wisdom R.; Lee C.; Dickson K.; Ruecroft G.; O'Brien F; Littlechild J; Bevan J.; Roberts S. M.; Evans C.T.; Tetrahedron Asymmetry., 1993, 4, 1117.
5. 4. Kam B.L.; Oppenheimer N.J., J.Org.Chem., 1981, 46, 3268.
6. 5. Katagiri N.; Ito Y.; Kitano K.; Toyota A.; Kaneko C.; Chem.Pharm. Bull., 1994, 42, 2653; Mahmodian M.; Baines B.S.; Dawson M.J.; Lawrence G.C.; Enzyme Microb. Technol., 1992, 14, 911.
7. 5. Katagiri N.; Ito Y.; Kitano K.; Toyota A.; Kaneko C.; Chem.Pharm. Bull., 1994, 42, 2653; Mahmodian M.; Baines B.S.; Dawson M.J.; Lawrence G.C.; Enzyme Microb. Technol., 1992, 14, 911.
8. 6 see Flynn D.L.; Zelle R.E.; Grieco P.A.; J. Org. Chem., 1983, 48, 2424.
9. 4), and concentrated under reduced pressure to give the acetonide 6 (117 mg, 40%)
10. 1H NMR spectrum where the protons at the carbon atoms bearing the acetonide are doublets since they couple only to each other and not to the other vicinal protons which are in in a trans relationship.
11. 9. Cieplak, A.S. J. Am. Chem. Soc., 1981, 103, 4540
12. 10. Toyota, A.: Ono, Y.; Kaneko, C. Tetrahedron Lett., 1995, 36, 6123.