29782-70-5Relevant academic research and scientific papers
Design of sulfides with a locked conformation as promoters of catalytic and asymmetric sulfonium ylide epoxidation
Davoust, Marion,Briere, Jean-Francois,Jaffres, Paul-Alain,Metzner, Patrick
, p. 4166 - 4169 (2005)
A new generation of 2,5-dimethylthiolanes with a locked conformation was developed to promote the asymmetric addition of chiral sulfonium ylides to aldehydes. The novel chiral sulfur derivative 4 succeeded the synthesis of trans-stilbene oxide derivatives with enantiomeric ratios ranging from 95:5 to 98:2. This user-friendly organocatalytic process proved to be efficient with 20-10% of sulfide 4 in 1 or 2 days of reaction. An insight into the ylide intermediate conformation is given on the basis of a computational ab initio study.
New camphor-derived selenonium ylides: Enantioselective synthesis of chiral epoxides
Li, Xin-Liang,Wang, Yi,Huang, Zhi-Zhen
, p. 749 - 752 (2007/10/03)
Optically pure selenonium salts 3 as the precursors of two new chiral selenonium ylides 4 can be synthesized stereoselectively from natural d-camphor in good yields. It is found that the reaction of the selenonium salt 3b, an aldehyde, and potassium tert-butoxide can take place smoothly in ?one-pot' via the formation of selenonium ylide 4b, to give chiral trans-diaryl epoxides 5 in good yields with good diastereoselectivities and enantioselectivities. CSIRO 2005.
