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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Enzymatic Amination for Stereocontrolled Functionalization of Cyclohexanones.

Juzhang Yan1,2, Jinping Bao1,2, Chengsen Cui1,3

  • 1State Key Laboratory of Engineering Biology for Low-Carbon Manufacturing, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, China.

Angewandte Chemie (International Ed. in English)
|March 26, 2025
PubMed
Summary

This study introduces an enzymatic reductive amination method using engineered imine reductases (IREDs) to stereoselectively synthesize chiral cyclohexylamines. This novel approach overcomes limitations in current chemical synthesis for creating complex cyclic amines.

Keywords:
Axial ChiralityBiocatalystChiral cyclohexylaminesCis/trans stereochemistryImine Reductase

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Area of Science:

  • Organic Chemistry
  • Biocatalysis
  • Stereoselective Synthesis

Background:

  • Achieving stereocontrol in functionalizing cyclohexanone's carbonyl carbon is synthetically challenging.
  • Existing methods for synthesizing cis/trans or axially chiral cyclohexanes are limited.
  • Stereocontrolled synthesis of 4-substituted cyclohexylamines is crucial for various applications.

Purpose of the Study:

  • To develop an enzymatic reductive amination strategy for stereoselective synthesis of cyclohexylamines.
  • To engineer imine reductase (IRED) M5 to achieve high stereocontrol in reductive amination.
  • To synthesize a diverse library of cis/trans and axially chiral 4-substituted cyclohexylamines.

Main Methods:

  • Enzymatic reductive amination using engineered imine reductase (IRED) M5.
  • Directed evolution and protein engineering of the IRED M5 enzyme pocket.
  • Stereoselective synthesis of over 80 distinct 4-substituted cyclohexylamines from corresponding cyclohexanones.

Main Results:

  • Successful engineering of IRED M5 variants for enhanced stereoselectivity.
  • Stereo-complementary synthesis of over 80 cis/trans and axially chiral 4-substituted cyclohexylamines.
  • Demonstrated industrial applicability and adherence to high standards in synthesis.

Conclusions:

  • Enzymatic reductive amination with engineered IREDs provides a powerful strategy for stereocontrolled synthesis of cyclohexylamines.
  • Enzyme pocket engineering enables selective binding and discrimination of imine precursors, leading to distinct stereochemical outcomes.
  • The proposed strategy holds potential for broader application in synthesizing diverse substituted cyclohexylamines.