Issue 5, 2021
From the journal:

Chemical Science

Kinetic resolution of racemic allylic alcohols via iridium-catalyzed asymmetric hydrogenation: scope, synthetic applications and insight into the origin of selectivity†

Haibo Wu, ORCID logo a   Cristiana Margarita,a   Jira Jongcharoenkamol,‡a   Mark D. Nolan, ORCID logo a   Thishana Singh ORCID logo b  and  Pher G. Andersson ORCID logo *ab  

* Corresponding authors

a Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, Stockholm, Sweden
E-mail: pher.andersson@su.se

b School of Chemistry and Physics, University of Kwazulu-Natal, Private Bag X54001, Durban, South Africa

Abstract

Asymmetric hydrogenation is one of the most commonly used tools in organic synthesis, whereas, kinetic resolution via asymmetric hydrogenation is less developed. Herein, we describe the first iridium catalyzed kinetic resolution of a wide range of trisubstituted secondary and tertiary allylic alcohols. Large selectivity factors were observed in most cases (s up to 211), providing the unreacted starting materials in good yield with high levels of enantiopurity (ee up to >99%). The utility of this method is highlighted in the enantioselective formal synthesis of some bioactive natural products including pumiliotoxin A, inthomycin A and B. DFT studies and a selectivity model concerning the origin of selectivity are presented.

Graphical abstract: Kinetic resolution of racemic allylic alcohols via iridium-catalyzed asymmetric hydrogenation: scope, synthetic applications and insight into the origin of selectivity

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Article information

DOI
https://doi.org/10.1039/D0SC05276K
Article type
Edge Article
Submitted
24 Sep 2020
Accepted
02 Dec 2020
First published
08 Dec 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 1937-1943

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Kinetic resolution of racemic allylic alcohols via iridium-catalyzed asymmetric hydrogenation: scope, synthetic applications and insight into the origin of selectivity

H. Wu, C. Margarita, J. Jongcharoenkamol, M. D. Nolan, T. Singh and P. G. Andersson, Chem. Sci., 2021, 12, 1937 DOI: 10.1039/D0SC05276K

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