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https://www.ias.ac.in/article/fulltext/jcsc/133/0028 -
Keywords
Sharpless asymmetric oxidation ;sulfide ;chiral sulfoxide. -
Abstract
While ortho-alkoxy aryl sulfoxides including various substituents were synthesized by Sharplessasymmetric oxidation reaction, we optimized the reaction conditions and screened better combination ofstarting materials to obtain high enantioselectivity. The result suggested new information that electron withdrawingsubstituents on the aromatic ring have a strong influence upon enantioselectivity of the products.Also, several chiral ligands for Sharpless asymmetric oxidation reaction were evaluated to improve theenantioselectivity.
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Graphical Abstract
High enantioselectivity of ortho-alkoxy aryl chiral sulfoxides have been achieved by Sharpless oxidation reaction using Ti(O-i-Pr)4 and diethyl tartrate under anhydrous condition. In particular, the enantioselctivity of products was influenced by electron-withdrawing substituents on the aromatic ring, such as nitro, ester and aldehyde groups.
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Author Affiliations
TAKANORI TAKEI1 JUN TAKAYAMA1 MEIYAN XUAN1 MISA TOMODA2 HIROSHI MIYAMAE2 TAKESHI SAKAMOTO1
- Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan
- Faculty of Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan
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Dates
- Published
- 11 March 2021
- Manuscript received
- 12 September 2020
- Manuscript revised
- 7 December 2020
- Accepted
- 20 December 2020
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Journal of Chemical Sciences
Volume 133, 2021
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