title: Lewis Acid Triggered Regioselective Magnesiation and Zincation of Uracils, Uridines, and Cytidines.
abstract: The Lewis acid MgCl2 allows control of the metalation regioselectivity of uracils and uridines. In the absence of the Lewis acid, metalation of uracil and uridine derivatives with TMPMgCl·LiCl occurs at the position C(5). In the presence of MgCl2, zincation using TMP2Zn·2LiCl·2MgCl2 occurs at the position C(6). This metalation method provides easy access to functionalized uracils and uridines. Using TMP2Zn·2LiCl·2MgCl2 also allows to functionalize cytidine derivatives at the position C(6).
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Lydia
authors.initials: L
authors.lastname: Klier
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Eider
authors.initials: E
authors.lastname: Aranzamendi
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Dorothée
authors.initials: D
authors.lastname: Ziegler
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Nickel
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Konstantin
authors.initials: K
authors.lastname: Karaghiosoff
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Carell
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D020650:Combinatorial Chemistry Techniques; D003562:Cytidine / Q000138:chemical synthesis / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015636:Magnesium Chloride / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014498:Uracil / Q000138:chemical synthesis / Q000737:chemistry*; D014529:Uridine / Q000138:chemical synthesis / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
chemical_list: D058116:Lewis Acids; D009942:Organometallic Compounds; C530465:TMPMgCl.LiCl; D015636:Magnesium Chloride; D014498:Uracil; D003562:Cytidine; D015032:Zinc; D014529:Uridine