The photochemical [2 + 2]-cycloadditions of 1,1-diethoxyethylene to chiral polyfunctional 2-cyclohexenones have been carried out leading to the production of highly constrained unusual α-amino acids with excellent regioselectivity and satisfactory yields. Theoretical calculations have been done to rationalize the observed regio- and diastereoselectivity and show that regiochemistry is determined by the relative rate of formation of the 1,4-biradical intermediates and not by the stability of these species.
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 20 Feb 2004|
García-Expósito, E., Álvarez-Larena, Á., Branchadell, V., & Ortuño, R. M. (2004). [2 + 2]-Photocycloaddition of 1,1-Diethoxyethylene to Chiral Polyfunctional 2-Cyclohexenones. Regioselectivity and π-Facial Discrimination. Journal of Organic Chemistry, 69(4), 1120-1125. https://doi.org/10.1021/jo035532n