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Issue 35, 2020
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Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres

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Abstract

Nucleophilic substitution reactions have always been considered as one of the most powerful reactions for the creation of carbon–carbon or carbon–heteroatom bonds in organic synthesis. In contrast to secondary carbons, the steric shielding of tertiary carbons retards a concerted, stereospecific nucleophilic substitution, and ionizing pathways often lead to nonselective substitution due to ion pair dissociation. In this minireview, we will detail pioneering contributions and more recent achievements emphasizing the feasibility of nucleophilic substitution on tertiary stereocentres under certain conditions, with inversion of configuration. The development of these transformations at tertiary centres are of remarkable added value to practitioners in the field of complex molecule synthesis. A stereoselective substitution at a quaternary carbon stereocentre with inversion of configuration is also discussed in the case of a three-membered ring.

Graphical abstract: Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres

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Article information


Submitted
06 May 2020
Accepted
28 Jul 2020
First published
28 Jul 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 9378-9385
Article type
Minireview

Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres

V. Lanke and I. Marek, Chem. Sci., 2020, 11, 9378
DOI: 10.1039/D0SC02562C

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