Highly enantioselective Biginelli reaction catalyzed by SPINOL-phosphoric acids

A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions with 5 mol% catalyst loading, a wide range of optically active dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 98%) with good to...

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Published inOrganic & biomolecular chemistry Vol. 10; no. 22; pp. 4467 - 4470
Main Authors Xu, Fangxi, Huang, Dan, Lin, Xufeng, Wang, Yanguang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.06.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions with 5 mol% catalyst loading, a wide range of optically active dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 98%) with good to excellent enantioselectivities (up to 99% ee). The synthetic utility of this method was demonstrated by the synthesis of chiral precursors of three drugs, including (S)-Monastrol, (S)-L-771688 and (S)-SQ 32926.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25663k