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Direct Asymmetric α‐Selective Mannich Reaction of β,γ‐Unsaturated Ketones with Cyclic α‐Imino Ester: Divergent Synthesis of Cyclocanaline and Tetrahydro Pyridazinone Derivatives.
- Source :
-
Chemistry - A European Journal . 3/17/2021, Vol. 27 Issue 16, p5130-5135. 6p. - Publication Year :
- 2021
-
Abstract
- The first regio‐, diastereo‐, and enantioselective direct Mannich reaction of β,γ,‐unsaturated ketones with benzoxazinone cyclic imines was enabled by Lewis acid/Brønsted base cooperative catalysis. The dinuclear zinc complex catalyzed the reaction of a broad range of β,γ‐unsaturated ketones to proceed at the α‐site exclusively, leading to corresponding adducts with two consecutive tertiary carbon stereocenters in diastereomeric ratios of up to >20:1 and enantioselectivities generally in the 90–99 % ee range. These products were used as general intermediates in the synthesis of multisubstituted cyclocanalines, tetrahydro pyridazinones, and 4H‐furo[2,3‐b][1,4]benzoxazine derivatives. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 27
- Issue :
- 16
- Database :
- Academic Search Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 149377363
- Full Text :
- https://doi.org/10.1002/chem.202100284