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Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

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.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Esters to β-Ketoesters: Claisen Condensation Mechanism

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the intermediate restores...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Metal-Ligand Bonds

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...

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Updated: Jun 6, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Published on: August 19, 2012

Assembling ligands in situ using bioorthogonal boronate ester synthesis.

Sung Bin Y Shin¹, Ramiro D Almeida, Guillermo Gerona-Navarro

¹Department of Pharmacology, Weill Medical College, Cornell University, New York, NY 10065, USA.

Chemistry & Biology

|November 25, 2010

Summary

Researchers developed a new bioorthogonal reaction for synthesizing large molecules from smaller parts within the body. This highly stable boronate ester (HiSBE) synthesis method offers a promising approach for drug development and cellular manipulation.

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Published on: November 30, 2022

Area of Science:

Chemical Biology
Organic Synthesis
Drug Discovery

Background:

Large molecules often face pharmacokinetic challenges, limiting their therapeutic potential.
Developing methods for in situ synthesis of complex molecules is crucial for advancing cellular manipulation.

Purpose of the Study:

To introduce a novel bioorthogonal reaction for synthesizing biologically active molecules.
To demonstrate the utility of this reaction in a physiological context using smaller precursors.

Main Methods:

Development and characterization of a highly stable boronate ester (HiSBE) synthesis.
Application of the HiSBE reaction for assembling a biologically active molecule in a physiological setting.

Main Results:

Successful synthesis of a biologically active molecule using the HiSBE reaction from smaller precursors.
Demonstration of the reaction's high stability and rapid rate in physiological conditions.

Conclusions:

The developed bioorthogonal HiSBE synthesis is a robust method for creating complex molecules in situ.
This approach holds significant potential for assembling diverse biologically active molecules within physiological environments, paving the way for new therapeutic strategies.