Investigation into the mechanism of the formation of (2S,6R/2R,6S)-1,1,3-triethoxycarbonyl-2,6,-di-(4-methoxyphenyl)cyclohex-3-en-4-ol

CHED 590

Kadye Ann Hill, khill1@angelo.edu, Bianca Baeza, janet.maxwell@angelo.edu, and Janet L. Maxwell, janet.maxwell@angelo.edu. Department of Chemistry and Biochemistry, Angelo State University, ASU Station #10892, San Angelo, TX 76909-0892
The synthesis of (2S,6R/2R,6S)-1,1,3-triethoxycarbonyl-2,6-di-(4-methoxyphenyl)cyclohex-3-en-4-ol was carried out with 4-(methoxybenzylidene) malonic acid diethyl ester and ethyl acetoacetate-1,3-13C2. Spectroscopic analysis of the 13C-labeled product gave strong evidence of two different competing reaction mechanisms.