Synthesis of Chiral Diazanedicarboxylates

Abstract

The potential of di-(–)-isobornyl diazenedicarboxylate (2) to act as a chiral azo-enophile in asymmetric ene reactions was investigated. Azo-enophile (2) was treated with trans-hex-3-ene and cyclohexene in the presence of tin(IV) chloride affording the ene adducts (4) and (5) respectively; however, no diastereoselectivity was observed. The synthesis of the novel chiral diazanedicarboxylates (12), (17) and (19) and the unsuccessful attempts to transform them into the chiral azo-enophiles (11), (16) and (19) bearing chiral oxazolidinone, diacetone-D-glucose and pantolactone chiral auxiliaries are also described.