Articles written in Journal of Chemical Sciences
Volume 133 All articles Published: 11 March 2021 Article ID 0028
A study of enantioselective syntheses by Sharpless asymmetric oxidation for aryl sulfoxides containing oxygen groups at the ortho position
TAKANORI TAKEI JUN TAKAYAMA MEIYAN XUAN MISA TOMODA HIROSHI MIYAMAE TAKESHI SAKAMOTO
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.
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.
Volume 135, 2023
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