Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

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Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids, Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes

Chemical Science ◽

10.1039/d1sc02061g ◽

2021 ◽

Author(s):

Eryn Nelson ◽

Jeffrey S. S. K. Formen ◽

Christian Wolf

Keyword(s):

Amino Acids ◽

Absolute Configuration ◽

Rapid Determination ◽

Amino Alcohols ◽

Enantioselective Synthesis ◽

Widespread Occurrence ◽

Chiral Compounds ◽

New Methods ◽

The Absolute

The widespread occurrence and significance of chiral compounds does not only require new methods for their enantioselective synthesis but also efficient tools that allow rapid determination of the absolute configuration,...

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Chirality Sensing of Amines, Diamines, Amino Acids, Amino Alcohols, and α-Hydroxy Acids with a Single Probe

Journal of the American Chemical Society ◽

10.1021/ja410428b ◽

2013 ◽

Vol 135 (48) ◽

pp. 18052-18055 ◽

Cited By ~ 89

Author(s):

Keith W. Bentley ◽

Yea G. Nam ◽

Jaslynn M. Murphy ◽

Christian Wolf

Keyword(s):

Amino Acids ◽

Amino Alcohols ◽

Hydroxy Acids ◽

Single Probe

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ChemInform Abstract: Chirospecific Synthesis of Amino Acids, Amino Aldehydes, and Amino Alcohols from D-Glucosamine Hydrochloride. A Multigram Synthesis of N-BOC-L-Serinal.

ChemInform ◽

10.1002/chin.199049269 ◽

1990 ◽

Vol 21 (49) ◽

Author(s):

A. GIANNIS ◽

T. HENK

Keyword(s):

Amino Acids ◽

Amino Alcohols ◽

Glucosamine Hydrochloride ◽

Amino Aldehydes

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N-Substituted α-trifluoromethyl β-nitro amines in the synthesis of fluorine-containing 1,2-diamines, amino alcohols, and β-amino acids

Russian Chemical Bulletin ◽

10.1007/s11172-009-0257-2 ◽

2009 ◽

Vol 58 (9) ◽

pp. 1886-1898 ◽

Cited By ~ 6

Author(s):

V. Yu. Korotaev ◽

A. Yu. Barkov ◽

M. I. Kodess ◽

I. B. Kutyashev ◽

P. A. Slepukhin ◽

...

Keyword(s):

Amino Acids ◽

Amino Alcohols

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ChemInform Abstract: Asymmetric Synthesis of Fluorine-Containing Amines, Amino Alcohols, α- and β-Amino Acids Mediated by Chiral Sulfinyl Group

ChemInform ◽

10.1002/chin.201021225 ◽

2010 ◽

Vol 41 (21) ◽

pp. no-no

Author(s):

Alexander E. Sorochinsky ◽

Vadim A. Soloshonok

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Amino Alcohols ◽

Sulfinyl Group

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Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Amino Alcohols

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19960288 ◽

1996 ◽

Vol 61 (2) ◽

pp. 288-297 ◽

Cited By ~ 1

Author(s):

Vladimír Pouzar ◽

Ivan Černý

Keyword(s):

Amino Acids ◽

Hydroxy Group ◽

Building Blocks ◽

Amino Alcohols ◽

New Approach ◽

Alternative Synthesis ◽

Oxime Derivatives ◽

A Chain ◽

Derivatives Of

New approach to the preparation of steroids with connecting bridge, based on an O-carboxymethyloxime (CMO) structure, and with terminal hydroxy group, is presented. 17-CMO derivatives of 3β-acetoxy- and 3β-methoxymethoxyandrost-5-en-17-one were condensed with α,ω-amino alcohols to give derivatives with a chain of seven to nine atoms. After THP-protection, these compounds were converted to 3-keto-4-ene derivatives. An alternative synthesis consisted in transformation of 17-CMO derivatives with bonded amino acids by reduction of the terminal carboxyl. The resulting compounds were designed as building blocks for the preparation of bis-haptens for sandwich immunoassays.

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