854049-19-7Relevant academic research and scientific papers
Enantioselective synthesis of (thiolan-2-yl)diphenylmethanol and its application in asymmetric, catalytic sulfur ylide-mediated epoxidation
Wu, Hsin-Yi,Chang, Chih-Wei,Chein, Rong-Jie
, p. 5788 - 5793 (2013/07/25)
This work describes an expeditious and efficient preparation of enantiopure (thiolan-2-yl)diphenylmethanol (2) featuring a double nucleophilic substitution and Shi epoxidation as key steps. One of the applications of its benzyl ether derivative to asymmetric sulfur ylide-mediated epoxidation with up to 92% ee (14 examples) was also demonstrated herein.
A new chiral organosulfur catalyst for highly stereoselective synthesis of epoxides
Gui, Yuan,Li, Jian,Guo, Chang-Shan,Li, Xin-Liang,Lu, Zhi-Feng,Huang, Zhi-Zhen
supporting information; experimental part, p. 2483 - 2487 (2009/09/08)
A new chrial organosulfide was synthesized through an unexpected Wagner-Meerwein rearrangement. This organosulfide could catalyze the epoxidation reaction of various aromatic aldehydes smoothly with benzyl bromide to give trans-diaryl epoxides in satisfactory yields (60-84%) with excellent diastereoselectivities (trans:cis=95:5-100:0) and good to excellent enantioselectivities (86-96% ee).
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.
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 (2007/10/03)
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.
