13113-71-8Relevant articles and documents
Optical Resolution of 2-Amino-1,2-diphenylethanol by Preferential Crystallization and Its Utilization in Fractional Crystallization and Enantioselective Reduction of Prochiral Ketones
Saigo, Kazuhiko,Ogawa, Shigeo,Kikuchi, Shigetoshi,Kasahara, Atsushi,Nohira, Hiroyuki
, p. 1568 - 1573 (1982)
(-/+)-erythro-2-Amino-1,2-diphenylethanol prepared from benzoin oxime by catalytic reduction was successfully resolved into pair of optically active forms by preferential crystallization.The optically active amino alcohol was found to be useful as a basic resolving agent for optical resolution of tartaric acid, trans-2,3-oxiranedicarboxylic acid, 2-hydroxy-2-phenylpropionic acid, and 3-endo-benzamido-5-norbornene-2-endo-carboxylic acid.Chiral hydrides prepared from lithium aluminium hydride and optical active threo- and erythro-2-amino-1,2-diphenylethanol derivatives were applied to the enantioface differentiating reduction of prochiral ketones to give the corresponding optically active alcohols in the 26-72percent optical purities.
Improved practical asymmetric synthesis of α-alkylmandelic acids utilizing highly diastereoselective alkylation of 5-aryl-2-(1-naphthyl)-1,3- dioxolan-4-ones
Misaki, Tomonori,Ureshino, Satoko,Nagase, Ryohei,Oguni, Yumiko,Tanabe, Yoo
, p. 500 - 504 (2006)
A practical method for the synthesis of optically pure α- alkylmandelic acids 1 is described. The present improved robust method involved two reactions: a mild, convenient, stereo-selective preparation of chiral cis-5-aryl-2-(1-naphthyl)-1,3-dioxolan-4-ones, 9a-c, and highly diastereoselective alkylation of 9a-c, followed by the hydrolysis.
Evaluation of dalbavancin as chiral selector for HPLC and comparison with teicoplanin-based chiral stationary phases
Zhang, Xiaotong,Bao, Ye,Huang, Ke,Barnett-Rundlett, Kimber L.,Armstrong, Daniel W.
, p. 495 - 513 (2010)
Dalbavancin is a new compound of the macrocyclic glycopeptide family. It was covalently linked to 5 lm silica particles using two different binding chemistries. Approximately 250 racemates including (a) heterocyclic compounds, (b) chiral acids, (c) chiral amines, (d) chiral alcohols, (e) chiral sulfoxides and sulfilimines, (f) amino acids and amino acid derivatives, and (g) other chiral compounds were tested on the two new chiral stationary phases (CSPs) using three different mobile phases. As dalbavancin is structurally related to teicoplanin, the same set of chiral compounds was screened on two commercially available teicoplanin CSPs for comparison. The dalbavancin CSPs were able to separate some enantiomers that were not separated by the teicoplanin CSPs and also showed improved separations for many racemates. However, there were other compounds only separated or better separated on teicoplanin CSPs. Therefore, the dalbavancin CSPs are complementary to the teicoplanin CSPs.
Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones
Keeri, Abdul Raheem,Gualandi, Andrea,Mazzanti, Andrea,Lewinski, Janusz,Cozzi, Pier Giorgio
supporting information, p. 18949 - 18952 (2016/01/26)
The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92 %), high enantioselectivities (up to 96 %), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.