A Convenient, One-Step Synthesis of Optically Active Tertiary Aminonaphthol and Its Applications in the Highly Enantioselective Alkenylations of Aldehydes

Abstract

Optically active tertiary aminonaphthol 1 was obtained by a new, convenient procedure and was found to catalyze the enantioselective alkenylation of various aldehydes with high ee values, which provides a practical method for the synthesis of chiral (E)- allyl alcohols.

Syntheses and Transformations of 1-(α-Aminobenzyl)-2-Naphthol Derivatives

“…31 Since the dimethylsubstituted Betti base 12a resulted in higher ee values in the enantioselective alkylation of benzaldehydes, attention focused on the preparation and examination of secondary 32,34,39 (Table 3, entries 5-10) and tertiary 34,39 ( The applicability of the tertiary aminonaphthols was extended by utilizing the addition of alkenylzinc to aldehydes (Scheme 17). 37 The best results are given in Table 4. Table 4.…”

Synthesis and conformational analysis of naphthylnaphthoxazine derivatives

“…The reaction can be extended by using chiral amines instead of ammonia, which furnishes non-racemic N-substituted aminonaphthol derivatives; this opened up a new area of application of these enantiopure compounds as chiral ligands in asymmetric transformations [3][4][5][6][7]. As a result of an integrated, virtual database screening, 7-[anilino(phenyl)methyl]-2-methyl-8-quinolinol was found to represent a promising new class of non-peptide inhibitors of the MDM2-p53 interaction [8].…”

Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour

“…Chiral Mannich bases of 2-naphthol are particularly popular in metal-mediated and ligand-accelerated catalysis of enantioselective carbon-carbon bond formation (11)(12)(13)(14)(15)(16)(17). Many of these carbon-carbon bond formation reactions involve the use of organozinc compounds as alkylating agents, which are relatively unreactive if uncoordinated (11).…”