29338-71-4Relevant articles and documents
Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols
Capel, Estefania,Rodríguez-Rodríguez, Marta,Uria, Uxue,Pedron, Manuel,Tejero, Tomas,Vicario, Jose L.,Merino, Pedro
supporting information, p. 693 - 707 (2022/01/04)
The catalyzed desymmetrizative ring expansion of alkenylcyclobutanols promoted by halofunctionalization of the alkene moiety with N-bromosuccinimide has been experimentally and computationally studied. The reaction yields highly enantioenriched cyclopenta
Asymmetric Nazarov Cyclizations of Unactivated Dienones by Hydrogen-Bond-Donor/Lewis Acid Co–Catalyzed, Enantioselective Proton-Transfer
Metternich, Jan B.,Reiterer, Martin,Jacobsen, Eric N.
, p. 4092 - 4097 (2020/09/01)
We report an enantioselective Nazarov cyclization catalyzed by chiral hydrogen-bond-donors in concert with silyl Lewis acids. The developed transformation provides access to tri-substituted cyclopentenones in high levels of enantioselectivity (up to 95% e.e.) from a variety of simple unactivated dienones. Kinetic and mechanistic studies are consistent with a reversible 4π-electrocyclization C?C bond-forming step followed by rate- and enantio-determining proton-transfer as the mode of catalysis. (Figure presented.).
Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion
Alazet, Sebastien,Preindl, Johannes,Simonet-Davin, Raphael,Nicolai, Stefano,Nanchen, Annik,Meyer, Thierry,Waser, Jerome
supporting information, p. 12334 - 12356 (2018/09/27)
Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.