Asymmetric catalytic synthesis of functionalized tetrahydroquinolines in supercritical fluids

• The first asymmetric organocatalytic domino-reaction in sc-fluids is accomplished.
• Useful tetrahydroquinolines are diastereo- and enantioselectively synthesized.
• Optimal quinine-derived bifunctional catalyst and sc-conditions are identified.

Bifunctional tertiary amine-catalysed Michael-initiated asymmetric domino-reactions are accomplished for the first time in supercritical fluids (sc-CO2 and sc-CHF3). In the proposed conditions, o-N-tosylaminophenyl α,β-unsaturated ketones react with α-nitroalkenes to afford valuable to pharmacology densely functionalized chiral tetrahydroquinolines in moderate to high yields and with very high diastereo- (dr > 99:1) and enantioselectivity (up to 98% ee).

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