Asymmetric counterion pair catalysis: An enantioselective Bronsted acid-catalyzed protonation

作者：Rueping Magnus^*; Theissmann Thomas; Raja Sadiya; Bats Jan W

来源：Advanced Synthesis & Catalysis, 2008, 350(7-8): 1001-1006.

DOI：10.1002/adsc.200800020

• BINOL phosphate
• enantioselective isomerization
• Hantzsch dihydropyridine
• organocatalytic cascade reaction
• transfer hydrogenation

A new asymmetric Bronsted acid-catalyzed cascade reaction involving a 1,4-addition, enantioselective protonation and 1,2-addition has been developed. This organocatalytic cascade not only provides for the first time 3- and 2,3-substituted tetrahydroquinolines and octahydroacridines in good yields with high dia- and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Bronsted acid-catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Bronsted acid-catalyzed hydride-proton-hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one-pot reaction sequence.

• 出版日期2008-5