95904-83-9Relevant academic research and scientific papers
High-Throughput Ligand Screening Enables the Enantioselective Conjugate Borylation of Cyclobutenones to Access Synthetically Versatile Tertiary Cyclobutylboronates
Clement, Helen A.,Boghi, Michele,McDonald, Rory M.,Bernier, Louise,Coe, Jotham W.,Farrell, William,Helal, Christopher J.,Reese, Matthew R.,Sach, Neal W.,Lee, Jack C.,Hall, Dennis G.
, p. 18405 - 18409 (2019)
Cyclobutane rings are important in medicinal chemistry, yet few enantioselective methods exist to access this scaffold. In particular, cyclobutylboronates are receiving increasing attention in the literature due to the synthetic versatility of alkylboronic esters and the increasing role of boronic acids in drug discovery. Herein, a conjugate borylation of α-alkyl,β-aryl/alkyl cyclobutenones is reported leading to the first synthesis of enantioenriched tertiary cyclobutylboronates. Cyclobutanones with two stereogenic centers are obtained in good to high yield, with high enantioselectivity and diastereoselectivity. Vital to this advance are the development of a novel approach to α,β unsymmetrically disubstituted cyclobutenone substrates and the use of a high-throughput chiral ligand screening platform. The synthetic utility of both the boronic ester and ketone functionalities is displayed, with remarkable chemoselectivity for either group being possible in this small ring scaffold.
VICINAL ALKYLATION OF ALKYNES. A SHORT ROUTE TOWARD Δα,β BUTENOLIDES, FURANS AND CYCLOPENTENONES.
Schmit, C.,Sahraoui-Taleb, S.,Differding, E.,Dehasse-De Lombaert, C. G.,Ghosez, L.
, p. 5043 - 5046 (2007/10/02)
Cyclobutenones 1 which are readily prepared from alkynes and keteniminium salts 2 were regiospecifically converted into Δα,β butenolides 4 or cyclopentenones 7.Reaction of 4 with diisobutylaluminium hydride yielded the corresponding substituted
