301191-47-9Relevant academic research and scientific papers
Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
Marcyk, Paul T.,Jefferies, Latisha R.,AbuSalim, Deyaa I.,Pink, Maren,Baik, Mu-Hyun,Cook, Silas P.
, 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.
Pseudoephenamine: A practical chiral auxiliary for asymmetric synthesis
Morales, Marvin R.,Mellem, Kevin T.,Myers, Andrew G.
, p. 4568 - 4571 (2012/06/30)
Unrestricted: Pseudoephenamine is introduced as a versatile chiral auxiliary and an alternative to pseudoephedrine in asymmetric synthesis. It is free from regulatory restrictions and leads to remarkable stereocontrol in alkylation reactions, especially in those that form quaternary carbon centers. Amides derived from pseudoephenamine exhibit a high propensity to be crystalline substances, and provide sharp, well-defined signals in NMR spectra. Copyright
Aminophosphine phosphinites derived from chiral 1,2-diphenyl-2-aminoethanols: Synthesis and application in rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives
Lou, Rongliang,Mi, Aiqiao,Jiang, Yaozhong,Qin, Yong,Li, Zhi,Fu, Fangmin,Chan, Albert S.C
, p. 5857 - 5863 (2007/10/03)
A series of chiral aminophosphine phosphinites DPAMPPs was synthesized from optically active 1,2-diphenyl-2-aminoethanols. The erythro-DPAMPPs were found to serve as excellent ligands for rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives. For an array of dehydroamino acid precursors, remarkably high enantioselectivity (up to 98.4% e.e.) and reactivity (the ratio of substrate/catalyst up to 10000) were observed. Some factors controlling the enantioselectivity were examined and discussed. (C) 2000 Elsevier Science Ltd.
