Highly Enantioselective Phenyl Transfer to Aryl Aldehydes Catalyzed by Easily Accessible Chiral Tertiary Aminonaphthol

Abstract

A new chiral tertiary aminonaphthol ligand 3b served as a highly efficient ligand for the asymmetric catalytic phenyl transfer to aromatic aldehydes and a variety of chiral diarylmethanols was prepared in high ee values (ee up to 99%) and chemical yields. The straightforward syntheses of both 3b and its enantiomer provide an excellent opportunity for large-scale applications.

Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C–C bond formations via the oxidative activation of sp 3 C–H bonds

“…We envisioned that a new type of Betti base (54, 55) would be formed through the CDC reaction of tetrahydroisoquinoline with 2-naphthol. Recently, chiral tertiary amino-naphthol ligands were shown to be highly enantioselective catalysts in phenyl transfer reactions (56). Indeed, the desired product 20 was obtained when tetrahydroisoquinoline was reacted with 2-naphthol under our CuBr͞TBHP system (Table 7, entry 3) in 58% NMR yield.…”

Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions

“…32 The bulkier naphthyl ring was inserted through the amine moiety when 2-naphthol (1) was aminoalkylated by using benzaldehyde (20c) and…”

“…By means of this reaction, a variety of chiral diarylmethanols were prepared with high (up to 99%) ee values and in high chemical yields. 32 Dahmen and Lormann highlighted the value of arylboranes as precursors for arylzinc reagents in asymmetric catalysis. On the application of 21a, the desired diarylmethanols were isolated with high (up to 98%) ee values.…”

Catalytic enantioselective arylations: boron to zinc exchange as a powerful tool for the generation of transferable aryl groups

“…39 The reaction is conducted under the same conditions as mentioned above with Bolm's catalyst 1 (Scheme 7), although the best enantioselectivity was obtained at -15 °C, in high yields and enantioselectivities. A similar chiral aminonaphtol ligand 18b was used by Dahmen and co-workers, to perform the arylation of aldehydes.…”