Syntheses of 1,2-Amino Alcohols and Their Applications for Oxazaborolidine Catalyzed Enantioselective Reduction of Aromatic Ketones

2007 ◽  
Vol 60 (3) ◽  
pp. 196 ◽  
Author(s):  
Namdev S. Vatmurge ◽  
Braja G. Hazra ◽  
Vandana S. Pore
Keyword(s):  
Amino Alcohol ◽  
Good Yield ◽  
Asymmetric Reduction ◽  
Enantiomeric Excess ◽  
Amino Alcohols ◽  
Secondary Alcohols ◽  
Aromatic Ketones ◽  
Enantioselective Reduction ◽  
Aryl Ketones

Six new chiral 1,2-amino alcohol derivatives have been synthesized starting from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. Asymmetric reduction of aryl ketones with in-situ generated oxazaborolidine from these amino alcohol derivatives and BH3·Me2S afforded secondary alcohols with good yield and moderate to high enantiomeric excess.

In Situ Measurement of the Enantiomeric Excess of Alcohols and Amines under Asymmetric Reduction Reaction by1H NMR

2010 ◽  
Vol 12 (14) ◽  
pp. 3238-3241 ◽  
Author(s):  
Xiaoxia Ye ◽  
Xinxiang Lei ◽  
Zhenfei Chen ◽  
Lixue Zhang ◽  
Anjiang Zhang
Keyword(s):  
Asymmetric Reduction ◽  
Enantiomeric Excess ◽  
Reduction Reaction ◽  
In Situ Measurement

Pd-catalyzed Arylation of 1,2-Amino Alcohol Derivatives via beta-Carbon Elimination

Synlett ◽  
2021 ◽  
Author(s):  
Ruben Martin ◽  
Miguel Pericàs ◽  
Miriam Sau
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Aryl Halides ◽  
Entry Point ◽  
New Entry

Herein, we describe a Pd-catalyzed arylation of 1,2-amino alcohols with aryl halides enabled by a retroallylation manifold. This protocol constitutes a new entry point to beta-arylated aldehydes via the intermediacy of in situ generated enamine intermediates. The protocol is characterized by its exquisite regioselectivity profile and broad substrate scope – including challenging substrate combinations –, even in an enantioselective manner

Enantioselective addition of ArTi(OiPr)3 to aldehydes catalyzed by a titanium complex of an N-sulfonylated amino alcohol

RSC Advances ◽  
2015 ◽  
Vol 5 (13) ◽  
pp. 9368-9373 ◽  
Author(s):  
Shih-Ju Chang ◽  
Shuangliu Zhou ◽  
Han-Mou Gau
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Secondary Alcohols ◽  
Titanium Catalyst ◽  
Titanium Complex ◽  
Enantioselective Addition ◽  
Asymmetric Additions

Asymmetric additions of ArTi(OiPr)3 to aldehydes catalyzed by a titanium catalyst of N-sulfonylated amino alcohols to afford desired secondary alcohols in good yields with good to excellent enantioselectivities of up to 95% ee.

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

scholarly journals Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl Ketones

Catalysts ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 671
Author(s):  
Chad M. Bernier ◽  
Joseph S. Merola
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantiomeric Excess ◽  
Transfer Hydrogenation ◽  
Acid Catalysts ◽  
Asymmetric Transfer Hydrogenation ◽  
Reaction Conditions ◽  
Chiral Complexes ◽  
Acetophenone Derivatives ◽  
Aryl Ketones

A series of chiral complexes of the form Ir(NHC)2(aa)(H)(X) (NHC = N-heterocyclic carbene, aa = chelated amino acid, X = halide) was synthesized by oxidative addition of -amino acids to iridium(I) bis-NHC compounds and screened for asymmetric transfer hydrogenation of ketones. Following optimization of the reaction conditions, NHC, and amino acid ligands, high enantioselectivity was achieved when employing the Ir(IMe)2(l-Pro)(H)(I) catalyst (IMe = 1,3-dimethylimidazol-2-ylidene), which asymmetrically reduces a range of acetophenone derivatives in up to 95% enantiomeric excess.

Arylation with Aryllead Triacetates Produced in situ by Mercury-Lead Exchange

1985 ◽  
Vol 38 (8) ◽  
pp. 1155 ◽  
Author(s):  
RP Kozyrod ◽  
JT Pinhey
Keyword(s):  
Good Yield ◽  
Lead Tetraacetate ◽  
Keto Ester ◽  
Rapid Formation

The addition of lead tetraacetate to diphenylmercury in chloroform leads to the rapid formation of a solution of phenyllead triacetate, which has been used directly for the C-phenylation of ethyl 2-oxocyclopentanecarboxylate (1) and 2-nitropropane in good yield. This method of arylation has been examined for a range of diorganolead compounds and the β-keto ester (1), and the results indicate that the method should be widely applicable.

ChemInform Abstract: Synthesis of 1,2- and 1,4-Amino Alcohols from 1,3-Dienes via Oxazines. Rearrangements of 1,4-Amino Alcohol Derivatives to Oxazolines.

ChemInform ◽  
2010 ◽  
Vol 41 (37) ◽  
pp. no-no
Author(s):  
Lukas Werner ◽  
Jason Reed Hudlicky ◽  
Martina Wernerova ◽  
Tomas Hudlicky
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols
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