144372-50-9Relevant academic research and scientific papers
Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp3-Hybridized Carbon Atoms: Kinetic Resolution of β-Amino Alcohols by p-Methoxybenzylation
Kuroda, Yusuke,Harada, Shingo,Oonishi, Akinori,Kiyama, Hiroki,Yamaoka, Yousuke,Yamada, Ken-Ichi,Takasu, Kiyosei
supporting information, p. 13137 - 13141 (2016/10/30)
A catalytic strategy was developed for asymmetric substitution reactions at sp3-hybridized carbon atoms by using a chiral alkylating agent generated in situ from trichloroacetimidate and a chiral phosphoric acid. The resulting chiral p-methoxybenzyl phosphate selectively reacts with β-amino alcohols rather than those without a β-NH functionality. The use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p-methoxybenzylation with good enantioselectivity.
The first synthesis of optically active 1-substituted taurines
Xu, Jiaxi,Xu, Shu,Zhang, Qihan
, p. 466 - 471 (2007/10/03)
Optically active 1-substituted taurines, a type of important sulfur analogues of naturally occurring amino acids, and their N-benzyloxycarbonyl- protected derivatives were synthesized from the corresponding optically active β-amino secondary alcohols in t
The use of pH to influence regio- and chemoselectivity in the asymmetric aminohydroxylation of styrenes
Nesterenko, Vitaliy,Byers, Joshua T.,Hergenrother, Paul J.
, p. 281 - 284 (2007/10/03)
(Matrix presented) The pH-controlled Sharpless asymmetric aminohydroxylation (AA) of styrenes provides 1-aryl-2-amino ethanols (regioisomer E enantio-, chemo-, and regioselectivity. As existing AA protocols typically give regioisomer A as the major reaction product when usin nitrogen sources, this method is a convenient alternative for the selective production of regioisomer B.
