Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands

作者：Moritani Junki; Hasegawa Yasuharu; Kayaki Yoshihito; Ikariya Takao^*

来源：Tetrahedron Letters, 2014, 55(6): 1188-1191.

DOI：10.1016/j.tetlet.2013.12.103

• Aerobic oxidation
• Bifunctional catalysts
• Asymmetric desymmetrization
• Meso-diols
• Lactonization

Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cp*Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions.

• 出版日期2014-2-5