Synthesis of enantiopure 2‐(aminoalkyl)phenol derivatives and their application as catalysts in stereoselective reactions

Abstract

Enantiopure 2-(aminoalkyl)phenol derivatives are an interesting class of compounds widely used in homogeneous ligand accelerated catalysis. A series of practical and convenient methods available for their preparation are revised, together with the methodologies for the determination of their configuration. The uses of these compounds in metal catalysed asymmetric reactions in the addition of dialkyl zinc reagents to aldehydes and in the reduction of ketones with borane are described. Moreover 2-(aminoalkyl)phenol derivatives have found use also as chiral shift reagents for carboxylic acids.

Scalable Synthesis of Interconnected Porous Silicon/Carbon Composites by the Rochow Reaction as High‐Performance Anodes of Lithium Ion Batteries

“…A particularly interesting group of (α‐phenylalkyl)amines contain ortho substituents like OH or OMe (with coordinating properties),15 CN16 or CO 2 R (as precursors of pharmacologically important isoindolin‐1‐ones)17 and halogens18 (susceptible to coupling, amidation or heteroatom addition reactions) 19. In particular, enantiomerically pure ortho ‐OH (or OMe) benzylamines and isoindolin‐1‐ones (readily obtained from ortho ‐CO 2 Me derivatives) with methyl groups at the benzyl position, have been used as chiral auxiliaries,20 ligands,21 or building blocks to prepare catalysts22 and biologically active compounds 23. In this field, derivatives that contain bulky substituents ( t Bu or i Pr) at the benzyl position have shown to be much more efficient in asymmetric catalysis,24 but they have not been widely used as chiral auxiliaries or ligands owing to the lack of natural sources and the absence of efficient asymmetric approaches to prepare them in optically pure form 25…”

Three-Component Betti Condensation for Synthesis of Aminomethylnaphthols Incorporating Deoxy-isoequilenine Scaffold-Absolute Configuration and Application

“…The configuration determination of the aminomethylnaphthols 5a/5b, 6a/6b, 8a and 9a/9b was of particular interest and was performed using NMR experiments. The 1 H and 13 C signals of the compounds were assigned by means of 1D and 2D spectra (distortionless enhancement by polarization transfer (DEPT), heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC) and nuclear overhauser effect spectroscopy (NOESY)). The implementation of the NOESY data was the approach applied 10,20,22 to obtain extensive information about the proton neighborhood around the newly formed stereogenic center at C-19.…”

“…11 The scope of the current knowledge on the synthesis and application of aminobenzylnaphthols has recently been demonstrated in review articles. [12][13][14][15][16][17] In most cases, various chiral amines are used in combination with different aldehydes to prepare chiral non-racemic aminobenzylnaphthols. [7][8][9]18,19 As a third component 2-naphthol is commonly used in the condensation reaction.…”

(+)-CSA Catalyzed Multicomponent Synthesis of 1-[(1,3-Thiazol-2-ylamino)methyl]-2-naphthols and Their Ring-Closure Reaction under Ultrasonic Irradiation

“…The Mannich reaction has also been performed to achieve stereoselective synthesis of aminonaphthol derivatives in the last decades. These stereoselective compounds have exhibited fairly good enantioselectivity in asymmetric reactions [17][18][19][20]. There are some reports on the use of heteroarylamines in Mannichtype reactions and synthesis of 2-amino-1,3-thiazoles in the literature [21][22][23][24][25][26].…”