In 1921 Levene and Mikeska, and in 1922 Noyes and Chiles prepared optically active esters in which the only asymetric carbon was that doubly bound to diazo nitrogen. The theoretical explanation being: that of the five valences of the nitrogen, four are covalences while the fifth is a Polar or ionizing valence. This may be illustrated by ammonium chloride.
Proceedings of the Iowa Academy of Science
©1929 Iowa Academy of Science, Inc.
Ray, F. E. and Bunting, W. R.
"The Decomposition of the Optically Active Diazo Ester from Aminolauronic Acid,"
Proceedings of the Iowa Academy of Science, 36(1), 271-274.
Available at: https://scholarworks.uni.edu/pias/vol36/iss1/63