Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 18, Pages 4452-4458Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100559
Keywords
Auto Tandem Catalysis; Asymmetric Catalysis; Kinetic Resolution; Organocatalysis; Meldrum's acid; 1; 3 prototropic shift
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Funding
- Centre National de la Recherche Scientifique (C.N.R.S) - french government
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A catalytic enantioselective vinylogous domino reaction has been successfully achieved, providing spirolactone dihydropyranones with high enantiomeric excess. The reaction involves an Auto Tandem Catalysis (ATC) process facilitated by the dual and complementary role of (DHQ)(2)PHAL organocatalyst, leading to good yields and high selectivity.
A catalytic enantioselective vinylogous domino reaction has been achieved from ketone-derived benzylidene Meldrum's acid and alpha-ketolactones to provide spirolactone dihydropyranones with more than 99% ee. An Auto Tandem Catalysis (ATC) process resulting from dual and complementary role of (DHQ)(2)PHAL organocatalyst resulted in a sequence involving an asymmetric vinylogous formal (4+2) cycloaddition of benzylidene and the subsequent kinetic resolution operating through a 1,3-prototropic shift leading to good yields (>50%) and the high selectivity.
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