949096-30-4Relevant academic research and scientific papers
Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols
Jiang, Yao,Schaus, Scott E.
, p. 1544 - 1548 (2017/02/05)
Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.
Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis
Piao, Fengnu,Mishra, Mithilesh Kumar,Jang, Doo Ok
, p. 7050 - 7055 (2012/08/28)
An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This m
Synthesis of enantiopure benzyl homoallylamines by indium-mediated barbier-type allylation combined with enzymatic kinetic resolution: Towards the chemoenzymatic synthesis of N-containing heterocycles
Hietanen, Ari,Saloranta, Tuna,Rosenberg, Sara,Laitinen, Evelina,Leino, Reko,Kanerva, Liisa T.
experimental part, p. 909 - 919 (2010/04/23)
Barbier-type indium-mediated allylations of different N, N(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields, The racemic amines were then subj
γ-Fluorophenyl-GABA derivatives from fluorobenzonitriles in high diastereomeric and enantiomeric excess
Ramachandran, P. Veeraraghavan,Reddy, G. Venkat,Biswas, Debanjan
experimental part, p. 204 - 215 (2009/07/18)
An enantioselective synthesis of α-fluoroaryl homoallylic amines in 52-71% yields and 76-93% enantioselectivities has been achieved via the allylboration of the corresponding fluorinated N-aluminobenzaldimines with B-allyldiisopinocampheylborane in the pr
Asymmetric synthesis of δ-substituted α,β-unsaturated δ-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines
Fiorelli, Claudio,Savoia, Diego
, p. 6022 - 6028 (2008/02/10)
(Chemical Equation Presented) Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl
Convenient synthesis of stable aldimine - Borane complexes, chiral δ-amino alcohols, and γ-substituted GABA analogues from nitriles
Ramachandran, P. Veeraraghavan,Biswas, Debanjan
, p. 3025 - 3027 (2008/02/10)
A one-pot synthesis of stable aldimine-trialkylborane adducts, the first synthesis of C- and N-deuterated imine-borane complexes, and their application for a highly enantioselective (84-99% ee) synthesis of δ-amino alcohols and γ-substituted γ-aminobutyri
