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Disubstituted Cyclohexanes: cis-trans Isomerism

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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

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Published on: May 27, 2015

Strategies for Accessing cis-1-Amino-2-Indanol.

Inès Mendas¹, Stéphane Gastaldi¹, Jean-Simon Suppo¹

¹Aix Marseille Univ, CNRS, ICR, Marseille, France.

Molecules (Basel, Switzerland)

|June 19, 2024

Summary

This review details methods for synthesizing cis-1-amino-2-indanol, a key chiral building block. It covers strategies for controlling cis-selectivity and enantioselectivity in its preparation.

Keywords:

C-H activation Ritter reaction chemical resolution cis-1-amino-2-indanol enantioselective reaction enzymatic resolution epimerization intramolecular cyclization

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Area of Science:

Organic Chemistry
Asymmetric Synthesis
Medicinal Chemistry

Background:

cis-1-amino-2-indanol is a crucial chiral building block.
It serves as a core structure in ligands, catalysts, chiral auxiliaries, and bioactive compounds.
Synthesis challenges include controlling cis-selectivity and enantioselectivity.

Purpose of the Study:

To review methodologies for synthesizing cis-1-amino-2-indanol.
To cover both racemic and enantioselective synthetic approaches.
To list substitution patterns on the aromatic ring and their preparation.

Main Methods:

Literature review of synthetic strategies over several decades.
Analysis of methods for achieving cis-selectivity.
Examination of enantioselective synthesis techniques.

Main Results:

Various synthetic routes for cis-1-amino-2-indanol have been developed.
Strategies effectively control cis-selectivity and enantioselectivity.
Different aromatic ring substitution patterns and their syntheses are cataloged.

Conclusions:

A comprehensive overview of cis-1-amino-2-indanol synthesis is provided.
The review facilitates the selection of appropriate methods based on desired selectivity.
It serves as a valuable resource for chemists working with this important molecule.