An example of a chiral non-racemic carbanion as versatile synthon in the asymmetric synthesis of polysubstituted γ-lactones
✍ Scribed by Carmen Ma Rodríguez; Miguel A. Ramírez; Victor S. Martín
- Book ID
- 104216074
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 242 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The application of a choral non-racemic carbanion generated from enantiomerically enriched a-sulfonyl-y-Iactones to the asymmetric synthesis of highly substituted and fused plactones is described.
The synthesis of butenolides and saturated y-lactones as optically active fragments is currently receiving considerable attention considering their utility as useful synthons for the synthesis of biologically active natural products.1 Very recently we have described a new approach to the stereocontrolled synthesis of such units in enantiomerically enriched form by an intramolecular Michael addition involving chiial non-racemic thiophenylacetates of y-hydroxy-@-unsaturated esters.2 This thermodynamically controlled process provided access to the all h-am substituted y-lactones with excellent stereocontrol.