[Efficient chiral control based on five-membered heterocyclic and related systems].
The synthetic potential of some simple five-membered heterocycles, including 2-oxazolone, 1,3-dihydro-2-imidazolone and 2-thiazolone as building blocks for chiral polyfunctional compounds as well as chiral heterocyclic auxiliaries for asymmetric synthesis is reviewed. The stereodefined introduction of easily replaceable groups to the 4,5-olefinic moiety of the 2-oxazolone ring to give versatile chiral synthons, followed by stereospecific and stepwise substitution, provides a working and versatile strategy for achieving a chiral synthesis, which leads to the preparation of a wide variety of 2-amino alcohols of biological interest. Sterically constrained chiral 2-oxazolidinones and the derived conformationally rigid amino alcohols, which are derived from cycloaddition reactions of the 2-oxazolone to cyclic dienes such as 9,10-dimethylanthracene and hexamethylcyclopentadiene, represent excellent chiral auxiliaries and chiral ligands which are of general use in asymmetric synthesis. The strategy developed using 2-oxazolone can also be used in the cases of the structurally similar 1,3-dihydro-2-imidazolone and 2-thiazolone derivatives.
Kunieda
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Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1, Oe-honmachi, Kumamoto 862-0973, Japan.
D002625:Chemistry, Organic / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010081:Oxazolone; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D010081:Oxazolone