Author:
Brimble Margaret A.,Duckworth Matthew S.,Lee Connie K. Y.
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.
Cited by
3 articles.
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