Revision of the stereochemistry of the reductive Heck cyclisation of 1-(2-iodobenzoyl)-4-substituted-1.4-dihydro-pyridine-3-carbaldehyde aminals

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5719-5722

  Mangeney, Pierre ^a   Pays, Christophe ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Chiral aminals; Dihydropyridines; Heck reactions; Isoindolone synthesis

Indexed keywords

1,4 DIHYDROPYRIDINE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; EPIMERIZATION; HECK REACTION; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0038166604     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01384-4     Document Type: Article

References (8)

1. Pays C., Mangeney P. Tetrahedron Lett. 42:2001;589-592.
2. Probably on a wrong sample.
3. We have always obtained regio and diastereoselective additions of alkyl copper reagents on acyl pyridinium salts derived from 6 . See: Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349-10362. In one case, with an ethoxyvinyl copper reagent, we have observed that the selectivities were dependent of the nature of the acyl chloride, see Ref. 3.
4. We have always obtained regio and diastereoselective additions of alkyl copper reagents on acyl pyridinium salts derived from 6 . See: Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349-10362. In one case, with an ethoxyvinyl copper reagent, we have observed that the selectivities were dependent of the nature of the acyl chloride, see Ref. 3.
5. Raussou S., Gosmini R., Mangeney P., Alexakis A., Commerçon M. Tetrahedron Lett. 35:1994;5433-5436.
6. Crystallographic data have been deposited at the Cambridge Data (no. CCDC 199720).
7. Crystallographic data have been deposited at the Cambridge Data (no. CCDC 199721).
8. 3).