Enantioselective Imine Reduction Catalyzed by Phosphenium Ions

2019 ◽  
Vol 141 (36) ◽  
pp. 14083-14088 ◽  
Author(s):  
Travis Lundrigan ◽  
Erin N. Welsh ◽  
Toren Hynes ◽  
Chieh-Hung Tien ◽  
Matt R. Adams ◽  
...  
Keyword(s):  
Phosphenium Ions ◽  
Imine Reduction

scholarly journals Mechanistic insight into B(C6F5)3 catalyzed imine reduction with PhSiH3 under stoichiometric water conditions

RSC Advances ◽  
2021 ◽  
Vol 11 (34) ◽  
pp. 20961-20969
Author(s):  
Yunqing He ◽  
Wanli Nie ◽  
Ying Xue ◽  
Qishan Hu
Keyword(s):  
Mechanistic Insight ◽  
Excess Water ◽  
Water Conditions ◽  
Imine Reduction ◽  
Water Amount ◽  
Insight Into

Hydrosilylation or amination products? It depends on water amount and nucleophiles like excess water or produced/added amines.

Unsymmetrically substituted N-heterocyclic phosphenium ions

2010 ◽  
Vol 13 (8-9) ◽  
pp. 998-1005 ◽  
Author(s):  
Dirk Schmid ◽  
Denis Bubrin ◽  
Daniela Förster ◽  
Martin Nieger ◽  
Eric Roeben ◽  
...  
Keyword(s):  
Phosphenium Ions

scholarly journals Insertion of Phosphenium Ions into a Bicyclo[1.1.0]Tetraphosphabutane Iron Complex

Molecules ◽  
2021 ◽  
Vol 26 (13) ◽  
pp. 3920
Author(s):  
Martin Weber ◽  
Gábor Balázs ◽  
Alexander V. Virovets ◽  
Eugenia Peresypkina ◽  
Manfred Scheer
Keyword(s):  
Diffraction Analysis ◽  
Room Temperature ◽  
31P Nmr ◽  
Spectroscopic Studies ◽  
Iron Complex ◽  
The Novel ◽  
X Ray Diffraction ◽  
X Ray ◽  
Phosphenium Ions

By reacting [{Cp‴Fe(CO)2}2(µ,η1:1-P4)] (1) with in situ generated phosphenium ions [Ph2P][A] ([A]− = [OTf]− = [O3SCF3]−, [PF6]−), a mixture of two main products of the composition [{Cp‴Fe(CO)2}2(µ,η1:1-P5(C6H5)2)][PF6] (2a and 3a) could be identified by extensive 31P NMR spectroscopic studies at 193 K. Compound 3a was also characterized by X-ray diffraction analysis, showing the rarely observed bicyclo[2.1.0]pentaphosphapentane unit. At room temperature, the novel compound [{Cp‴Fe}(µ,η4:1-P5Ph2){Cp‴(CO)2Fe}][PF6] (4) is formed by decarbonylation. Reacting 1 with in situ generated diphenyl arsenium ions gives short-lived intermediates at 193 K which disproportionate at room temperature into tetraphenyldiarsine and [{Cp‴Fe(CO)2}4(µ4,η1:1:1:1-P8)][OTf]2 (5) containing a tetracyclo[3.3.0.02,7.03,6]octaphosphaoctane ligand.

Iridicycle-Catalysed Imine Reduction: An Experimental and Computational Study of the Mechanism

2015 ◽  
Vol 21 (46) ◽  
pp. 16564-16577 ◽  
Author(s):  
Hsin-Yi Tiffany Chen ◽  
Chao Wang ◽  
Xiaofeng Wu ◽  
Xue Jiang ◽  
C. Richard A. Catlow ◽  
...  
Keyword(s):  
Computational Study ◽  
Imine Reduction

A New Class of Low-Loading Catalysts for Highly Enantioselective, Metal-Free Imine Reduction of Wide General Applicability

ChemCatChem ◽  
2017 ◽  
Vol 9 (6) ◽  
pp. 941-945 ◽  
Author(s):  
Davide Brenna ◽  
Riccardo Porta ◽  
Elisabetta Massolo ◽  
Laura Raimondi ◽  
Maurizio Benaglia
Keyword(s):  
General Applicability ◽  
Metal Free ◽  
New Class ◽  
Imine Reduction

scholarly journals Fates of imine intermediates in radical cyclizations of N-sulfonylindoles and ene-sulfonamides

2015 ◽  
Vol 11 ◽  
pp. 1649-1655 ◽  
Author(s):  
Hanmo Zhang ◽  
E Ben Hay ◽  
Stephen J Geib ◽  
Dennis P Curran
Keyword(s):  
Carbonyl Group ◽  
Ring Opening ◽  
Radical Cyclizations ◽  
Type Reaction ◽  
Primary Products ◽  
Lactam Carbonyl Group ◽  
Lactam Carbonyl ◽  
Imine Reduction ◽  
Derivatives Of

Two new fates of imine intermediates formed on radical cyclizations of ene-sulfonamides have been identified, reduction and hydration/fragmentation. Tin hydride-mediated cyclizations of 2-halo-N-(3-methyl-N-sulfonylindole)anilines provide spiro[indoline-3,3'-indolones] or spiro-3,3'-biindolines (derived from imine reduction), depending on the indole C2 substituent. Cyclizations of 2-haloanilide derivatives of 3-carboxy-N-sulfonyl-2,3-dihydropyrroles also presumably form spiro-imines as primary products. However, the lactam carbonyl group facilitates the ring-opening of these cyclic imines by a new pathway of hydration and retro-Claisen-type reaction, providing rearranged 2-(2'-formamidoethyl)oxindoles.

Protic additives or impurities promote imine reduction with pinacolborane

2019 ◽  
Vol 17 (7) ◽  
pp. 1999-2004 ◽  
Author(s):  
Blake S. N. Huchenski ◽  
Alexander W. H. Speed
Keyword(s):  
Reduction Reactions ◽  
Imine Reduction

We report here that addition of stoichiometric amounts of alcohols or water to mixtures of imines and pinacolborane promote reduction reactions.

ChemInform Abstract: PHOSPHORUS HETEROCYCLE SYNTHESIS USING PHOSPHENIUM IONS AND 1,4-DIENES

1984 ◽  
Vol 15 (25) ◽  
Author(s):  
A. H. COWLEY ◽  
C. A. STEWART ◽  
B. R. WHITTLESEY ◽  
T. C. WRIGHT
Keyword(s):  
Heterocycle Synthesis ◽  
Phosphenium Ions
Sign in / Sign up

Export Citation Format

Share Document