60754-49-6Relevant articles and documents
Fritsch-Buttenberg-Wiechell rearrangement in the aliphatic series
Rezaei,Yamanoi,Chemla,Normant
, p. 419 - 421 (2000)
(Formula presented) Substituted vinylidene zinc carbenoids undergo a Fritsch-Buttenberg-Wiechell rearrangement. The migratory aptitude of the two groups R/R1 was studied by 13C labeling experiments and depends on the degree of substi
The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis
Sun, Wencheng,Teng, Qiaoling,Cheng, Dongping,Li, Xiaonian,Xu, Xiaoliang
supporting information, (2019/12/05)
Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.
Catalytic Enantioselective Synthesis of 1,4-Keto-Alkenylboronate Esters and 1,4-Dicarbonyls
Liang, Michael Z.,Meek, Simon J.
supporting information, p. 14234 - 14239 (2019/08/30)
A catalytic enantioselective method for the synthesis of 1,4-keto-alkenylboronate esters by a rhodium-catalyzed conjugate addition pathway is disclosed. A variety of novel, bench-stable alkenyl gem-diboronate esters are synthesized. These easily accessible reagents react smoothly with a collection of cyclic α,β-unsaturated ketones, generating a new C?C bond and stereocenter. Products are isolated in up to 99 % yield with greater than 20:1 E/Z and greater than 99:1 e.r. Mechanistic studies show the site-selectivity of transmetalation and reactivity is ligand dependent. The utility of the approach is highlighted by gram-scale synthesis of enantioenriched cyclic 1,4-diketones, and stereoselective transformations of the products by hydrogenation, allylation, and isomerization.
