1 3
Topics in Current Chemistry (2019) 377:23
4 Combination of Cu with CPAs
4.1 Cyclizations
Cascade cycloisomerization reactions between carbonyl, imine, and alkenyl group
or alkynyl group have provided a versatile tool for synthesis of heterocyclic scaffolds. In 2011, Toste’s group developed a tandem cycloisomerization reaction for
synthesis of furan derivatives 54 by using a chiral anionic copper(II) phosphonate
catalyst (Scheme 16) [54]. Heterocyclization of 2-(1-alkynyl)-2-alkene-1-ones 53
followed by nucleophilic attack by indoles 43 yields products 54 with a high level of
enantioselectivity (72–93% ee).
Scheme 15 Asymmetric iron-catalyzed Paal–Knorr reaction of 1,4-diones and anilines
Scheme 16 Cu-catalyzed enantioselective cycloisomerization–indole addition reactions
Reprinted from the journal
165
Topics in Current Chemistry (2019) 377:23
4 Combination of Cu with CPAs
4.1 Cyclizations
Cascade cycloisomerization reactions between carbonyl, imine, and alkenyl group
or alkynyl group have provided a versatile tool for synthesis of heterocyclic scaffolds. In 2011, Toste’s group developed a tandem cycloisomerization reaction for
synthesis of furan derivatives 54 by using a chiral anionic copper(II) phosphonate
catalyst (Scheme 16) [54]. Heterocyclization of 2-(1-alkynyl)-2-alkene-1-ones 53
followed by nucleophilic attack by indoles 43 yields products 54 with a high level of
enantioselectivity (72–93% ee).
Scheme 15 Asymmetric iron-catalyzed Paal–Knorr reaction of 1,4-diones and anilines
Scheme 16 Cu-catalyzed enantioselective cycloisomerization–indole addition reactions
Reprinted from the journal
165