Alkaloids-catalyzed regio- and enantioselective allylic nucleophilic substitution of tert-butyl carbonate of the Morita-Baylis-Hillman products

Tetrahedron Letters

Volumn 45, Issue 25, 2004, Pages 4967-4971

  Du, Yishu ^a   Han, Xiuling ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ALKALOID; CARBONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; SUBSTITUTION REACTION;

EID: 2942519744     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.135     Document Type: Article

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41. The alkaloid derivative TQO used as the catalyst was synthesized according to the known procedure: See Ref. [2p], in which the same compound was named as QD-4. We use the name TQO as in Ref. [3a]
42. General procedure for alkaloid catalyzed allylic nucleophilic substitution of (4): To a solution of ethyl (2-methylidene-3-tert- butoxycarbonyloxy)phenyl-propanoate (4) (0.1 mmol) and pronucleophile (0.12 mmol) in dry toluene (2 mL) was added alkaloid (0.02 mmol), the reaction mixture was stirred at room temperature overnight and purified by silica gel column chromatography to obtain the product