146539-23-3Relevant academic research and scientific papers
Dynamic Kinetic Resolution of Alkenyl Cyanohydrins Derived from α,β-Unsaturated Aldehydes: Stereoselective Synthesis of E-Tetrasubstituted Olefins
Majhi, Jadab,Turnbull, Ben W. H.,Ryu, Ho,Park, Jiyong,Baik, Mu-Hyun,Evans, P. Andrew
, p. 11770 - 11774 (2019/08/16)
A novel dynamic kinetic resolution (DKR) of tetrasubstituted alkenyl cyanohydrins prepared from the corresponding α,β-unsaturated aldehydes is described. The deprotonation of a geometrical mixture of tetrasubstituted alkenyl cyanohydrins with sodium diiso
Contiguous Quaternary Centers from a AuI-Catalyzed Nazarov Cyclization
Congmon, Jonathan,Tius, Marcus A.
supporting information, p. 2926 - 2930 (2018/06/27)
The cationic AuI-catalyzed cyclization of highly substituted enynes has been shown to provide cyclopentenones with up to two contiguous, all-carbon atom quaternary centers in a diastereospecific process. In the more challenging examples in whic
Lewis acid-promoted rearrangement of 2,3-epoxy alcohol derivatives: Stereochemical control and selective formation of two types of chiral quaternary carbon centers from the single carbon skeleton
Kita, Yasuyuki,Matsuda, Satoshi,Inoguchi, Ryoko,Ganesh, Jnaneshwara K.,Fujioka, Hiromichi
, p. 5191 - 5197 (2007/10/03)
The Lewis acid-promoted rearrangement of 2,2,3,3-tetrasubstituted 2,3-epoxy alcohols with several kinds of protecting groups was investigated. When SnCl4 is used as a Lewis acid, the reaction proceeds in a regio- and stereo-controlled manner to
The Diastereoselectivity of Electrophilic Attack on Trigonal Carbon Adjacent to a Stereogenic Centre: Diastereoselective Protonation, Epoxidation and Acylation of Allylsilanes
Fleming, Ian,Lewis, Jeremy J.
, p. 3267 - 3276 (2007/10/02)
The four allylsilanes 6 and 8, which have a stereogenic centre carrying a phenyl group, a methyl group and a hydrogen atom adjacent to the nucleophilic end of the double bond, react with protic (or deuteronic) acid, m-chloroperbenzoic acid and chlorosulfonyl isocyanate to give eletrophilic substitution of the allylsilane, with diastereoselectivity in the sense 2, in conformity to a general rule for electrophilic attack on a double bond adjacent to a stereogenic centre.The most reliably stereoselective reactions took place with the allylsilane 6b, in which the stereogenic centre is cis to a group larger than a hydrogen atom in both the E- and Z-isomer.In general, chlorosulfonyl isocyanate induces higher stereoselectivity than the peracid, and the peracid higher stereoselectivity than the proton (or deuteron).
