1. Benzotetramisole catalyzed kinetic resolution of 2h-azirines.
Qiupeng Peng, Bei Zhang, Lala Liu, Donghui Guo, Jian Wang. Chem Commun (Camb). 2020 Oct 21; 56(82): 12427-12430. DOI: 10.1039/d0cc05379a. PMID: 32939521.
An unprecedented benzotetramisole (BTM)-catalyzed kinetic resolution for the efficient synthesis of chiral 2H-azirines is described. This protocol provides two chiral isomers in one step with broad scope, good yield and high enantioselectivity. In addition, the optically pure 2H-azirine products have proven to be useful building blocks for further synthetic transformations.
2. Benzotetramisole-catalyzed dynamic kinetic resolution of azlactones.
Xing Yang, Guojian Lu, Vladimir B Birman. Org Lett. 2010 Feb 19; 12(4): 892-5. DOI: 10.1021/ol902969j. PMID: 20099896.
Enantioselective acyl transfer catalyst benzotetramisole (BTM) has been found to promote dynamic kinetic resolution of azlactones providing di(1-naphthyl)methyl esters of alpha-amino acids with up to 96% ee.
3. Benzotetramisole: a remarkably enantioselective acyl transfer catalyst.
Ximin Li, Vladimir B Birman. Org Lett. 2006 Mar 30; 8(7): 1351-4. DOI: 10.1021/ol060065s. PMID: 16562889.
[reaction: see text] A commercially available pharmaceutical, tetramisole, was found to be a competent enantioselective acylation catalyst. Its benzannellated analogue, benzotetramisole (BTM), produced outstanding enantioselectivities in kinetic resolution of secondary benzylic alcohols.
