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Ruthenium(II)/Chiral Brønsted Acid Co-Catalyzed Enantioselective Four-Component Reaction/Cascade Aza-Michael Addition for Efficient Construction of 1,3,4-Tetrasubstituted Tetrahydroisoquinolines.
- Source :
- Chemistry - A European Journal; Feb2014, Vol. 20 Issue 6, p1505-1509, 5p
- Publication Year :
- 2014
-
Abstract
- An elegant synergistic catalytic system comprising a ruthenium complex with a chiral Brønsted acid was developed for a four-component Mannich/cascade aza-Michael reaction. The ruthenium-associated ammonium ylides successfully trapped with in situ generated imines indicates a stepwise process of proton transfer in the ruthenium-catalyzed carbenoid NH insertion reaction. The different decomposition abilities of various ruthenium complexes towards diazo compounds were well explained by the calculated thermodynamic data. The transformation features a mild, rapid, and efficient method for the synthesis of enantiomerically pure 1,3,4-tetrasubstituted tetrahydroquinolines bearing a quaternary stereogenic carbon center from simple starting precursors in moderate yields with high diastereo- and enantioselectivity. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 20
- Issue :
- 6
- Database :
- Complementary Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 94181874
- Full Text :
- https://doi.org/10.1002/chem.201304576