Petschen, I., Borsh, M.P., & Guerrero, A. 2000 Enzyme-catalyzed synthesis and absolute configuration of (1S,2R,5S)- and (1R,2S,5R)-2-(1-hydroxyethyl)-1- (methoxymethyloxyethyl)cyclobutane- 1-carbonitri le, key intermediates for the preparation of chiral cyclobutane-containiing pheromones.. Tetrahedron: Assymetry 11(8): 1691-1695.
Notes: Formal synthesis of chiral grandisol and the oleander scale pheromone (Aspidiotus nerii) and their antipodes can be achieved through a convenient lipase-catalyzed nantiodifferentiation process of the common cyclobutane intermediate (+/-)-2-(l-hydroxyethyl)-1-(methoxymethyl) cyclobutane-1-carbonitrile 3. The resolution afforded both enantiomers in almost enantiomerically pure form and their absolute configurations were assigned on the basis of the Delta delta values for their (R)- and (S)-MTPA esters.