Lewis acid-catalyzed reactions of ethyl diazoacetate with aldehydes. Synthesis of α-formyl esters by a sequence of aldol reaction and 1,2- nucleophilic rearrangement

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5055-5058

  Kanemasa, Shuji ^a   Kanai, Toshio ^a   Araki, Takahiro ^a   Wada, Eiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033516531     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00932-6     Document Type: Article

References (30)

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26. 4 and evaporated in vacuo. The residue was chromatographed on silica gel with hexane - diethyl ether (8:1 v/v) to give a mixture of formyl ester 3 and b-keto ester 4.
27. 2 giving 50% yield of 4a.
28. See Note 13 for the evidence for the reversibility of reaction of 1 with 2.
29. When this reaction is performed in diethyl ether, the desilylated derivative of 5 is selectively formed (Kanemasa, S.; Araki, T.; Kanai, T.; Wada, E. Tetrahedron Lett. 1999, 40, 5059-5062.
30. p- Anisaldehyde is produced in 40% yield, indicating the possible reversibility of reaction of 1 with 2.