51547-88-7Relevant articles and documents
Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Br?nsted acid catalyst
Takagi, Ryukichi,Sakai, Yuichiro,Duong, Duyen Thi
, (2021/03/23)
A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Br?nsted acid. Computational prediction of the pKa value of BSI indicated its classification as a strong Br?nsted acid. BSI catalyzed the h
Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
Marcyk, Paul T.,Jefferies, Latisha R.,AbuSalim, Deyaa I.,Pink, Maren,Baik, Mu-Hyun,Cook, Silas P.
supporting information, p. 1727 - 1731 (2019/01/21)
The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.
A simple stereoselective synthesis of enantiopure 2-substituted pyrrolidines and piperidines from chiral (R)-phenylglycinol-derived bicyclic 1,3-oxazolidines
Andres, Jose M.,Herraiz-Sierra, Ignacio,Pedrosa, Rafael,Perez-Encabo, Alfonso
, p. 1719 - 1726 (2007/10/03)
Chiral, nonracemic 2-substituted pyrrolidines and piperidines were prepared in high ee and moderate to good chemical yields in three steps from (R)-phenylglycinol and γ- or δ-chloroketones. The key step of the synthesis was the stereo- selective reductive ring-opening of chiral bicyclic 1,3- oxazolidines prepared by condensation of (R)-phenylglycinol and the corresponding ketones.
