Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur‐Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation. Issue 1 (22nd November 2017)

• Record Type: Journal Article
• Authors: Li, Jian‐Ping; Tuo, Hao‐Ran; Xie, Ming‐Sheng; Kang, Bo; Qu, Gui‐Rong; Guo, Hai‐Ming
• Is Part Of: Asian journal of organic chemistry. Volume 7:Issue 1(2018)
• Page Start: 128
• Page End: 132
• Publication Date: 2017-11-22
• Subjects: enantioselectivity -- nucleosides -- organocatalysis -- organosulfur compounds -- pyrimidines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700533
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A direct route to chiral pyrimidine acyclic nucleoside analogues with a sulfur‐containing side chain is reported via enantioselective tandem conjugated addition‐protonation reactions of thioacetic acid to α‐pyrimidine substituted acrylates. In the presence of a quinine‐derived thiourea catalyst, diverse chiral sulfur‐containing pyrimidine acyclic nucleoside analogues could be obtained in excellent yields (95–99 %) and with moderate to excellent enantioselectivity values (up to 99 % ee ). Abstract : AdPro : A direct route to chiral pyrimidine acyclic nucleoside analogues with a sulfur‐containing side chain has been reported via enantioselective tandem conjugated addition/protonation reactions of thioacetic acid to α‐pyrimidine substituted acrylates. In the presence of a quinine‐derived thiourea catalyst, diverse chiral sulfur‐containing pyrimidine acyclic nucleoside analogues were formed in excellent yields (95–99 %) and moderate to excellent enantioselectivities (up to 99 % ee ).