Kinetic resolution of sterically hindered secondary alcohols catalyzed by aminophosphinite organocatalyst. Issue 2 (11th January 2018)

• Record Type: Journal Article
• Authors: Hara, Nanami; Fujisawa, Shu; Fujita, Mizuki; Miyazawa, Mikako; Ochiai, Kazuma; Katsuda, Satoshi; Fujimoto, Tetsuya
• Is Part Of: Tetrahedron. Volume 74:Issue 2(2018)
• Page Start: 296
• Page End: 302
• Publication Date: 2018-01-11
• Subjects: Kinetic resolution -- Secondary alcohol -- Benzoylation -- Organocatalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.11.062
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Kinetic resolution of secondary alcohols by benzoylation using a phosphinite derivative of (1 S, 2 R )-1-amino-2-indanol as the catalyst was investigated. The aminophosphinite catalyst is effective for the kinetic resolution of aryl cycloalkyl carbinols with a small number of examples for organocatalytic kinetic resolution to achieve resolution with s = up to 44. Although the benzoylation of phenylalkanols proceeded with a low selectivity, 1-arylalkanols bearing at least one substituent at the ortho position on the benzene ring or a branched alkyl group on the carbinol carbon were resolved with acceptable selectivity. Graphical abstract: