In 1921, Levene and Mikeska, and in 1922, Noyes and Chiles prepared optically active esters in which the only possible asymmetric carbon was that doubly bound to diazo nitrogen. Due to this double bond being semipolar the nitrogen loses an electron to the carbon. The asymmetry of the carbon atom would result from the localization of this electron much the same as the localization of the ordinary bond is considered to cause asymmetry.
Proceedings of the Iowa Academy of Science
©1930 Iowa Academy of Science, Inc.
Ray, Francis Earl and Hemphill, Martha G.
"Decomposition of Optically Active Diazo Compounds,"
Proceedings of the Iowa Academy of Science, 37(1), 235-236.
Available at: https://scholarworks.uni.edu/pias/vol37/iss1/44