599165-40-9Relevant articles and documents
Arene-catalysed lithiation of triflates and triflamides under Barbier-type conditions: An indirect transformation of alcohols and amines into organolithium compounds
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
, p. 14341 - 14348 (1996)
The reaction of alkyl triflates 1 or benzyl triflamides 3 with an excess of lithium powder and a catalytic amount of naphthalene (4 mol%) in the presence of different electrophiles [Me3SiCl, Pr(i)CHO, Bu(t)CHO, PhCHO, 4-MeOC6H4-CHO, CH3(CH2)6CHO, Et2CO, (CH2)5CO, (c-C3H5)2CO, PhCOMe, 4-MeC6H4COPh, PhCh=NPh, n-C8H7CON(CH2)4] in THF at temperature ranging between -78 and 0°C leads, after hydrolysis with water, to the corresponding condensation products 2. When α,β-unsaturated carbonyl compounds are used as electrophilic compounds 1,2- (3-cyclohexenone) or 1,4-addition (cinnamaldehyde or benzylideneacetone) takes place depending on the electrophile used.
Guanidine–Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates
Ge, Yicen,Cui, Xi-Yang,Tan, Siu Min,Jiang, Huan,Ren, Jingyun,Lee, Nicholas,Lee, Richmond,Tan, Choon-Hong
supporting information, p. 2382 - 2386 (2019/02/01)
An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine–copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an SN2′ borylation process catalyzed by a monodentate guanidine–copper(I) complex that proceeds through a special direct enantioconvergent transformation mechanism.
TARTROL-derived chiral phosphine-phosphite ligands and their performance in enantioselective Cu-catalyzed 1,4-addition reactions
Dindaroglu, Mehmet,Akyol, Sema,Simsir, Hamza,Neudoerfl, Joerg-Martin,Burke, Anthony,Schmalz, Hans-Guenther
, p. 657 - 662 (2013/07/11)
By using (R,R,R,R)-2,3-dimethoxy-2,3-dimethyl-1,4-dioxane-5,6-bis- diphenylmethanol (TARTROL) as a chiral building block, a set of six modular phosphine-phosphite ligands (with a 1,2-phenylene backbone) were synthesized and evaluated in the Cu-catalyzed a
