Synthesis of some new tertiary amines and their application as co-catalysts in combination with l-proline in enantioselective Baylis-Hillman reaction between o-nitrobenzaldehyde and methyl vinyl ketone

Tetrahedron Letters

Volumn 47, Issue 32, 2006, Pages 5717-5721

  Tang, Hongying ^a   Zhao, Guofeng ^a   Zhou, Zhenghong ^a   Zhou, Qilin ^a   Tang, Chuchi ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE DERIVATIVE; CYCLOHEXANE OXIDE; CYCLOHEXANOL DERIVATIVE; CYCLOHEXENE DERIVATIVE; KETONE DERIVATIVE; PHENETHYLAMINE DERIVATIVE; PROLINE; PYRAZINE DERIVATIVE; TERTIARY AMINE;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; METHYLATION; RING OPENING; SEPARATION TECHNIQUE; SYNTHESIS;

EID: 33745601363     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.023     Document Type: Article

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47. General procedure for the chiral amine/l-proline co-catalyzed reaction: To a solution of aldehyde (2 mmol), chiral amine and l-proline in 2.5 mL of solvent was added MVK (6 mmol). Then the resulting mixture was stirred at 20 °C for completion of the reaction (monitored by TLC). After removal of solvent, the residue was purified by column chromatography on silica gel (200-300 mesh, gradient eluted with petroleum ether/ethyl acetate) to afford the product.