ChemInform Abstract: Catalytic Asymmetric Epoxidation of Aldehydes. Optimization, Mechanism, and Discovery of Stereoelectronic Control Involving a Combination of Anomeric and Cieplak Effects in Sulfur Ylide Epoxidations with Chiral 1,3-Oxathianes.
✍ Scribed by V. K. AGGARWAL; J. G. FORD; S. FONQUERNA; H. ADAMS; R. V. H. JONES; R. FIELDHOUSE
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 35 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Catalytic Asymmetric Epoxidation of Aldehydes. Optimization, Mechanism, and Discovery of Stereoelectronic Control Involving a Combination of Anomeric and Cieplak Effects in Sulfur Ylide Epoxidations with Chiral 1,3-Oxathianes. -The chiral sulfide (CTH) is an efficient catalyst for the asymmetric epoxidation of aldehydes. High diastereo-and enantioselectivities are observed for aromatic and unsaturated aldehydes, whereas with aliphatic aldehydes moderate yields and stereoselectivities are obtained. The stereoselectivity depends on steric as well as electronic (anomeric and Cieplak) effects as is shown by formation of the epoxide (IIIa) in the presence of different sulfides. -(AGGARWAL, V. K.; FORD,