(1R,2S)-2-Amino-1,2-diphenylethanol

A solid-state fluorescent host system with a 2(1)-helical column consisting of chiral (1R,2S)-2-amino-1,2-diphenylethanol and fluorescent 1-pyrenecarboxylic acid.[Pubmed:18293291]

Chem Asian J. 2008 Mar 7;3(3):625-629.

A solid-state fluorescent host system was created by self-assembly of a 2(1)-helical columnar organic fluorophore composed of (1R,2S)-2-Amino-1,2-diphenylethanol and fluorescent 1-pyrenecarboxylic acid. This host system has a characteristic 2(1)-helical columnar hydrogen- and ionic-bonded network. Channel-like cavities are formed by self-assembly of this column, and various guest molecules can be included by tuning the packing of this column. Moreover, the solid-state fluorescence of this host system can change according to the included guest molecules. This occurs because of the change in the relative arrangement of the pyrene rings as they adjust to the tuning of the packing of the shared 2(1)-helical column, according to the size of the included guest molecules. Therefore, this host system can recognize slight differences in molecular size and shape.

A solid-state fluorescence sensing system consisting of chiral (1R,2S)-2-amino-1,2-diphenylethanol and fluorescent 2-anthracenecarboxylic acid.[Pubmed:17650013]

Org Lett. 2007 Aug 16;9(17):3457-60.

A solid-state fluorescence sensing system was created by using a chiral supramolecular organic fluorophore having a channel-like cavity composed of (1R,2S)-2-Amino-1,2-diphenylethanol as a chiral molecule and 2-anthracenecarboxylic acid as a fluorescence molecule.

Efficient crystallization-induced dynamic resolution of alpha-substituted carboxylic acids.[Pubmed:15176855]

J Org Chem. 2004 Jun 11;69(12):4256-61.

Herein we present a novel route to enantiomerically enriched chiral alpha-substituted carboxylic acids by crystallization-induced dynamic resolution (CIDR) of their diastereomeric salts with chiral amines. Thus, the racemic alpha-bromo acid 3 is converted reliably with (1R,2S)-2-Amino-1,2-diphenylethanol in the presence of a catalytic amount of tetrabutylammonium bromide into its R-enantiomer 4 in 90% yield with 88% ee. Similarly, the racemic alpha-thiobenzoyl acid 5 could be resolved to 90% ee in 74% yield. Further enrichment to enantiomeric homogeneity could be achieved in both cases by crystallization. In a telescoped, two-step process, S-alpha-thiobenzoyl acid 6 (>or=99.6% ee) was prepared from the racemic bromide 3 in 63% yield. State-of-the-art parallel experimentation enabled rapid screening for suitable dynamic resolution conditions. Kinetic studies defined the influence of temperature, tetrabutylammonium bromide concentration, molarity, and solvent polarity on the resolution rate, product yield, and enantiomeric excess.

An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: serendipity rules.[Pubmed:12074650]

Org Lett. 2002 Jun 27;4(13):2133-6.

[reaction: see text] Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-Amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.

Asymmetric synthesis of [2,3-(13)C(2),(15)N]-4-benzyloxy-5,6-diphenyl-2,3,5,6-tetrahydro-4H-oxazine-2-one via lipase TL-mediated kinetic resolution of benzoin: general procedure for the synthesis of [2,3-(13)C(2),(15)N]-L-alanine.[Pubmed:11722198]

J Org Chem. 2001 Nov 30;66(24):8010-4.

Lipase TL-mediated kinetic resolution of benzoin proceeded to give the corresponding optically pure (R)-benzoin (R)-1. On the other hand, (S)-benzoin O-acetate (S)-7 could be hydrolyzed without epimerization to give (S)-benzoin (S)-1 under alkaline conditions. Furthermore, both enantiomers of benzoin (1) were converted to [(15)N]-(1R,2S)- and (1S,2R)- 2-amino-1,2-diphenylethanol (3a and 3b), respectively, according to the procedure reported previously. [2,3-(13)C(2),(15)N]-(5S,6R)-4-benzyloxy-5,6-diphenyl-2,3,5,6-tetrahydro-4H-oxazi ne-2-one (10) was synthesized from ethyl [1,2-(13)C(2)]bromoacetate and (1R,2S)-2-Amino-1,2-diphenylethanol (3b) in three steps. Finally, [2,3-(13)C(2),(15)N]-L-alanine (12) was prepared via alkylation of the lactone 10 and hydrogenation of the alkylated product 11.