SYNTHESIS OF CHIRAL DIAZANEDICARBOXYLATES

Authors
BRIMBLE MA DUCKWORTH MS LEE CKY
Citation
Ma. Brimble et al., SYNTHESIS OF CHIRAL DIAZANEDICARBOXYLATES, Australian Journal of Chemistry, 51(10), 1998, pp. 907-913
Citations number
20
Categorie Soggetti
Chemistry
Journal title
Australian Journal of Chemistry → ACNP
ISSN journal
00049425
Volume
51
Issue
10
Year of publication
1998
Pages
907 - 913
Database
ISI
SICI code
0004-9425(1998)51:10<907:SOCD>2.0.ZU;2-K
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) res pectively; however, no diastereoselectivity was observed. The synthesi s of the novel chiral diazanedicarboxylates (12), (17) and (19) and th e unsuccessful attempts to transform them into the chiral azo-enophile s (11), (16) and (19) bearing chiral oxazolidinone, diacetone-D-glucos e and pantolactone chiral auxiliaries are also described.