Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes

Hong-Cheng Shen; Yu-Feng Wu; Ying Zhang; Lian-Feng Fan; Zhi-Yong Han; Liu-Zhu Gong

doi:10.1002/anie.201712350

Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes

Angew Chem Int Ed Engl. 2018 Feb 23;57(9):2372-2376. doi: 10.1002/anie.201712350. Epub 2018 Feb 6.

Authors

Hong-Cheng Shen¹, Yu-Feng Wu², Ying Zhang¹, Lian-Feng Fan¹, Zhi-Yong Han¹, Liu-Zhu Gong^{1

3}

Affiliations

¹ Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.
² School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, 150001, China.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China.

PMID: 29336513
DOI: 10.1002/anie.201712350

Abstract

A Pd^II -catalyzed asymmetric aminohydroxylation of 1,3-dienes with N-tosyl-2-aminophenols was developed by making use of a chiral pyridinebis(oxazoline) ligand. The highly regioselective reaction provides direct and efficient access to chiral 3,4-dihydro-2H-1,4-benzoxazines in high yield and enantioselectivity (up to 96:4 e.r.). The reaction employs readily available N-tosyl-2-aminophenols as a unique aminohydroxylation reagent and is complementary to known asymmetric aminohydroxylation methods.

Keywords: aminohydroxylation; asymmetric catalysis; aza-Wacker reactions; benzoxazines; palladium.

Publication types

Research Support, Non-U.S. Gov't