A remarkable stereocontrol during cobalt(II) chloride catalysed opening of cinnamoyl epoxides with N-substituted anilines

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8379-8382

  De, Asit ^a   Ghosh, Shubhajit ^a   Iqbal, Javed ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; ANILINE DERIVATIVE; CINNAMYL ALCOHOL; COBALT CHLORIDE; EPOXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0030670590     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10171-X     Document Type: Article

References (5)

1. (a) Bhatia, B.; Jain, S.; De, A.; Bagchi, I.; Iqbal, J. Tetrahedron Lett. 1996, 37, 7311.
2. (b) Punniyamurthy, T.; Iqbal, J. Tetrahedron Lett. 1997, 38, 4466.
3. (c) Das, B.C.; Iqbal, J. Tetrahedron Lett. 1997, 38, 2903.
4. Experimental Procedure: The epoxide (5 mmol) (prepared according to reference 1a) was dissolved in acetonitrile (20 ml) and dry cobalt(II) chloride (5 mol%) was added to this solution. The resulting mixture was stirred under nitrogen atmosphere for 5 to 6 hrs at ambient temperature. Removal of solvent gave a residue which was taken in ethyl acetate (50 ml) and washed with saturated solution of sodium bicarbonate and water. Drying (magnesium sulphate) and removal of the solvent gave a residue which was chromatographed over silica gel (hexane-ethyl acetate) to afford the amino alcohols.
5. 3): 7.35-7.16 (m,5H), 6.95 (d, J=6.5Hz, 4H), 6.82 (d, J=10Hz, 2H), 6.5 (d, J=10Hz, 2H), 4.95 (d, J=6.7Hz. 1H), 4.65 (dd, J1=J2=6.7Hz, 1H), 4.4 (d, J=16.65Hz. 1H), 4.10 (m, 3H), 3.64 (s, 3H), 2.7 (d, J=6.7Hz, 1H), 2.18 (s, 3H), 1.14 (t, J=8.9Hz, 3H). 5a: 7.44-7.07 (m, 12H), 6.90-6.69 (m, 3H), 5.45 (d, J=6.7Hz, 1H), 4.9 (d, J=16.6Hz, 1H), 4.83 (dd, J1=J2=6.7Hz, 1H), 4.59 (d, J=16.6Hz, 1H), 4.14 (q, J=7Hz, 2H), 2.83 (d, J=6.7Hz, 1H), 1.16 (t, J=8.9Hz, 3H). FAB mass (m/e, relative intensity): 3d: 420 [(m+1), 30%], 316 [(m-103), 100%] and 105 [(m-314), 70%]. 5a: 376 [(m+1), 80%], 272 [(m-103), 100%], 182 [(m-193), 70%] and 91 [(m-284),100%].