Preparation of chiral 1-phenylethanols and bromides

1985 ◽  
Vol 63 (12) ◽  
pp. 3442-3448 ◽  
Author(s):  
Allan R. Stein ◽  
Robert D. Dawe ◽  
James R. Sweet
Keyword(s):  
General Procedure ◽  
Optical Purity ◽  
Secondary Alcohols ◽  
One Pot ◽  
Convenient Procedure ◽  
Optical Rotations ◽  
Nmr Methods ◽  
Substituted 1

A fast, convenient procedure for preparing and resolving moderate to large quantities of chiral secondary alcohols is described. The general procedure involves a one-pot conversion of the ketone (various acetophenones) to the half-ester of a diacid (succinic, phthalic… ) and resolution with (+)- and (−)-1-phenylethylamines. Overall yields of the enantiomeric alcohols, the variously substituted 1-phenylethanols, are generally 65–85% with optical purities of approximately 90%. Properties and optical rotations of a number of chiral 1-phenylethanols and of the bromides made from them are tabulated. A discussion of optical purity determinations using nmr methods is included and absolute configurations are reported.

scholarly journals Demonstration of Redox Potential ofMetschnikowia koreensisfor Stereoinversion of Secondary Alcohols/1,2-Diols

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
Vachan Singh Meena ◽  
Linga Banoth ◽  
U. C. Banerjee
Keyword(s):  
Substrate Specificity ◽  
Redox Potential ◽  
Optical Purity ◽  
Cofactor Regeneration ◽  
High Yield ◽  
Secondary Alcohols ◽  
One Pot ◽  
Wide Range ◽  
Multistep Reaction

The present work reports theMetschnikowia koreensis-catalyzed one-pot deracemization of secondary alcohols/1,2-diols and their derivatives with in vivo cofactor regeneration. Reaction is stereoselective and proceeds with sequential oxidation of (R)-secondary alcohols to the corresponding ketones and the reduction of the ketones to (S)-secondary alcohols. Method is applicable to a repertoire of racemic aryl secondary alcohols and 1,2-diols establishing a wide range of substrate specificity ofM. koreensis. This ecofriendly method afforded the product in high yield (88%) and excellent optical purity (>98%ee), minimizing the requirement of multistep reaction and expensive cofactor.

One-Pot Protocol for Synthesis of α-Organosulfonyloxy Ketones from Secondary Alcohols Using Hypervalent Iodine(V)–Mediated Oxidations

2009 ◽  
Vol 39 (17) ◽  
pp. 3101-3110 ◽  
Author(s):  
Swapnil S. Deshmukh ◽  
Sameerana N. Huddar ◽  
Krishnacharya G. Akamanchi
Keyword(s):  
Hypervalent Iodine ◽  
Secondary Alcohols ◽  
One Pot

ChemInform Abstract: A Mild One-Pot Method for Conversion of Various Steroidal Secondary Alcohols into the Corresponding Olefins.

ChemInform ◽  
2011 ◽  
Vol 42 (51) ◽  
pp. no-no ◽  
Author(s):  
Raju Ranjith Kumar ◽  
Shrutisagar Dattatraya Haveli ◽  
Henri B. Kagan
Keyword(s):  
Secondary Alcohols ◽  
One Pot

One-pot synthesis of 1-substituted 1H-1,2,3,4-tetrazoles from 2aminothiazoles using tributylmethylammonium chloride as a catalyst

2017 ◽  
Vol 23 (5) ◽  
Author(s):  
Kerru Nagaraju ◽  
Gummidi Lalitha ◽  
Parvesh Singh ◽  
Chunduri Venkata Rao
Keyword(s):  
Sodium Azide ◽  
Triethyl Orthoformate ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted 1

AbstractReaction between substituted thiazolylamine or oxazolylamine, triethyl orthoformate and sodium azide in the presence of tributylmethylammonium chloride in DMSO furnishes 1-substituted 1

scholarly journals Synthesis, Characterization and Anticancer Evaluation of Nitrogen Substituted 1-(3-Aminoprop-1-ynyl)-4-Hydroxyanthraquinone Derivatives

2021 ◽  
Author(s):  
Nafisa S. Sirazhetdinova ◽  
Dmitry S Baev ◽  
Victor A. Savelyev ◽  
Tatyana S. Golubeva ◽  
Lyubov S. Klimenko ◽  
...  
Keyword(s):  
Cancer Cells ◽  
Sonogashira Reaction ◽  
Secondary Amines ◽  
One Pot ◽  
Standard Drug ◽  
Three Component Reaction ◽  
G Quadruplex ◽  
New Compounds ◽  
Substituted 1 ◽  
Mcf 7

Abstract Anthraquinones are of significant interest due to their biological activity, coloring properties and synthetic applications. Here, we describe a mild and convenient method for modification of 1-ethynyl-4-hydroxyanthraquinone that was obtained from the Sonogashira reaction of 1-hydroxy-4-iodoanthraquinone with alkynes. The copper(I) catalyzed one-pot three component reaction (A3-coupling) of the new 1-ethynyl-4-hydroxyanthraquinone with secondary amines and formaldehyde was the main approach for the synthesis of nitrogen substituted 1-[3-(amino)prop-1-ynyl]-4-hydroxyanthraquinones. The influence of different substituent in the amine on reaction rate and yield has been evaluated. The cytotoxicity of 1-ethynyl-4-hydroxyanthraquinones was evaluated using the conventional MTT assay. Among all the compounds synthesized, anthraquinone-propargylamine derivatives 28, 29, 30 and 34 possess most promising cytotoxic potential towards glioblastoma cancer cells; compounds 14 and 19 shown selectivity towards the prostate cancer cells DU-145, and 18, and 24 – towards breast cancer cells MCF-7. The grown inhibition on these cancer cells of 18 and 24 was comparable to those of standard drug Doxorubicin. Molecular modeling of new compounds in DNA G-quadruplex binding site was performed to help understand the observed SAR trends.

A novel inorganic–organic nanohybrid material H4SiW12O40/pyridino-MCM-41 as efficient catalyst for the preparation of 1-amidoalkyl-2-naphthols under solvent-free conditions

2015 ◽  
Vol 44 (20) ◽  
pp. 9596-9609 ◽  
Author(s):  
R. Tayebee ◽  
M. M. Amini ◽  
M. Akbari ◽  
A. Aliakbari
Keyword(s):  
Solvent Free ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
The One ◽  
Substituted 1 ◽  
Nanohybrid Material ◽  
Mcm 41

A new inorganic–organic nanohybrid material was prepared and performed as an efficient catalyst for the one-pot multi-component synthesis of different substituted 1-amidoalkyl-2-naphthols under solvent-free conditions.

One Pot Tandem Dual C=C and C=O Bond Reductions in β-Alkylation of Secondary Alcohols with Primary Alcohols by Ruthenium Complexes of Amido and Picolyl Functionalized N-Heterocyclic Carbenes

2021 ◽  
Author(s):  
A. P. Prakasham ◽  
Sabyasachi Ta ◽  
Shreyata Dey ◽  
Prasenjit Ghosh
Keyword(s):  
Ruthenium Complexes ◽  
Heterocyclic Carbenes ◽  
Secondary Alcohols ◽  
Coupling Reactions ◽  
Primary Alcohols ◽  
One Pot ◽  
The One ◽  
Alcohol Alcohol

Two different class of ruthenium complexes, namely, [1-mesityl-3-(2,6-Me2-phenylacetamido)-imidazol-2-ylidene]Ru(p-cymene)Cl (1c) and {[1-(pyridin-2-ylmethyl)-3-(2,6-Me2-phenyl)-imidazol-2-ylidene]Ru(p-cymene)Cl}Cl (2c), successfully carried out the one-pot tandem alcohol-alcohol coupling reactions of a variety of secondary and primary alcohols, in...

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