title: A simple method for α-position deuterated carbonyl compounds with pyrrolidine as catalyst.
abstract: A simple, cost-effective method for deuteration of carbonyl compounds employing pyrrolidine as catalyst and D2O as deuterium source was described. High degree of deuterium incorporation (up to 99%) and extensive functional group tolerance were achieved. It is the first time that secondary amines are used as catalysts for H/D exchange of carbonyl compounds, which also allow the deuteration of complex pharmaceutically interesting substrates. A possible catalytic mechanism, based on the hydrolysis of 1-pyrrolidino-1-cyclohexene, for this pyrrolidine-catalyzed H/D exchange reaction has been proposed.
authors.affiliation: State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu, 610041, China.
authors.forename: Miao
authors.initials: M
authors.lastname: Zhan
authors.forename: Tao
authors.initials: T
authors.lastname: Zhang
authors.forename: Haoxi
authors.initials: H
authors.lastname: Huang
authors.forename: Yongmei
authors.initials: Y
authors.lastname: Xie
authors.forename: Yuanwei
authors.initials: Y
authors.lastname: Chen
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D053138:Cyclohexenes / Q000737:chemistry*; D017666:Deuterium Oxide / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: C585851:1-pyrrolidino-1-cyclohexene; D053138:Cyclohexenes; D011759:Pyrrolidines; D017666:Deuterium Oxide
keywords: chemoselectivity; deuterium; deuterium oxide; isotope exchange; ketones; pyrrolidine