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Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.

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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

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Published on: January 17, 2020

Effector enhanced enantioselective hydroformylation.

Shao-Tao Bai¹, Alexander M Kluwer², Joost N H Reek³

¹Homogeneous, Supramolecular and Bio-inspired Catalysis, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam (UvA), Science Park 904, 1098 XH Amsterdam, The Netherlands. j.n.h.reek@uva.nl.

Chemical Communications (Cambridge, England)

|November 9, 2019

Summary

This summary is machine-generated.

Chiral rhodium complexes with integrated receptors enhance enantioselective hydroformylation when bound to effectors. This supramolecular approach significantly boosts selectivity in rhodium-catalyzed reactions.

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Area of Science:

Organometallic Chemistry
Catalysis
Supramolecular Chemistry

Background:

Rhodium-DIMPhos complexes are key catalysts in hydroformylation.
Achieving high enantioselectivity in hydroformylation remains a challenge.
Supramolecular control offers a potential strategy for catalyst enhancement.

Purpose of the Study:

To develop rhodium DIMPhos complexes with integrated receptors for carboxylate-containing effectors.
To investigate the application of these supramolecular complexes in rhodium-catalyzed hydroformylation.
To evaluate the impact of effector binding on regio- and enantioselectivity.

Main Methods:

Synthesis of rhodium DIMPhos complexes featuring an integrated DIM-receptor.
Binding of achiral and chiral carboxylate-containing effectors to the supramolecular complex.
Application of the modified catalysts in the hydroformylation of vinyl acetate.
Analysis of reaction products for regio- and enantioselectivity (ee, b/l ratios).

Main Results:

The binding of achiral or chiral effectors significantly enhanced enantioselectivity compared to non-complexed catalysts.
A supramolecular complex ([Rh]/[1S⊂L3]) achieved high regio- and enantioselectivity (72% ee, b/l >99) in vinyl acetate hydroformylation.
Non-chiral [Rh(DIMPhos)] catalysts with chiral effectors did not induce enantioselectivity.

Conclusions:

Integrated DIM-receptors in rhodium DIMPhos complexes enable supramolecular control over catalysis.
Effector binding is crucial for enhancing enantioselectivity in chiral rhodium-metal complexes.
This supramolecular strategy provides a powerful tool for optimizing regio- and enantioselective hydroformylation.