105581-82-6Relevant articles and documents
Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: A chiral ammonium borinate catalysis
Pawliczek, Martin,Hashimoto, Takuya,Maruoka, Keiji
, p. 1231 - 1235 (2018)
Herein, we report the first alkylative kinetic resolution of vicinal alcohols realized by cooperative use of a chiral quaternary ammonium salt and an achiral borinic acid. In addition, a catalytic regioselective alkylation of a secondary alcohol in the presence of an unprotected primary one is presented, emphasizing the unique selectivity and potential of this ammonium borinate catalysis.
One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole
Christoffers, Jens,R??ler, Ulrich
, p. 654 - 658 (2007/10/03)
Ο-Allylations and Ο-benzylations of α-hydroxy esters (3a-3c) are performed without racemization. The reagents applied, Ο-allyl- and Ο-benzyltrichloroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.
Oxirane Ring-Opening with Alcohol Catalyzed by Organotin Phosphate Condensates. Complete Inversion at Tertiary and Benzylic Centers
Otera, Junzo,Niibo, Yoshihisa,Nozaki, Hitosi
, p. 7625 - 7634 (2007/10/02)
Regio- and stereospecific ring-opening of chiral oxiranes has been effected by organotin phosphate condensates catalyst.Alcohols attack on the tertiary and benzylic positions exclusively.Despite seemingly acidic character of the catalyst in terms of regioselectivity the chiral centers are completely inverted.The new methodology is applied to synthesis of enantiomerically pure linalool and to conversion of commercially available (R)-styrene oxide into the (S)-counterpart.