Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition

6533b823fe1ef96bd127f51c

RESEARCH PRODUCT

Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition

Xiang-yu Chen Qiang Liu Kari Rissanen Tao Shu Carolina Von Essen Dieter Enders Sun Li

subject

aromaattiset yhdisteet 010402 general chemistry 01 natural sciences Desymmetrization Catalysis Stereocenter Catalysis Direct entry Materials Chemistry ta116 kemiallinen synteesi 010405 organic chemistry Chemistry aromatic compounds Metals and Alloys Enantioselective synthesis General Chemistry Combinatorial chemistry 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Intramolecular force Ceramics and Composites Michael reaction Esterification reaction chemical synthesis

description

The first example of an N-heterocyclic carbene-catalyzed asymmetric desymmetrization of enal-tethered cyclohexadienones via an intramolecular homoenolate Michael addition/esterification reaction is described. This new protocol offers a direct entry to various functionalized tetrahydrofluorenones with three contiguous stereocenters in high yields, good diastereoselectivities and excellent enantioselectivities.

year	journal	country	edition	language
2018-06-23	Chemical Communications

https://doi.org/10.1039/c8cc04145h

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