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Synthesis 2021; 53(24): 4559-4566
DOI: 10.1055/a-1560-5245
DOI: 10.1055/a-1560-5245
short review
Transition-Metal-Catalyzed Enantioselective α-Arylation of Carbonyl Compounds to Give Tertiary Stereocenters
The Department of Chemical Sciences of the University of Padova is thankfully acknowledged for a grant (P-DiSC#08BIRD2019) and for a post-doctoral fellowship (E.-C.M.).
Abstract
Enantioenriched α-aryl carbonyl compounds are ubiquitous in natural products and biologically active compounds. Their synthesis has been explored over the last few decades and several methods now exist that allow for the enantioselective formation of a C(sp3)-C(sp2) bond in the α-position to a carbonyl group. However, although the formation of quaternary stereocenters has been fairly well established, the enantioselective formation of tertiary stereocenters proved more challenging due to facile product post-reaction racemization. In this short review, we summarize the methods reported to date for the asymmetric α-arylation of enolates and analogues that rely on transition-metal catalysis.
1 Introduction
2 Nucleophile Pre-activation
3 Activation via Aminocatalysis
4 Formation of Constrained Stereocenters
5 Concluding Remarks
Key words
α-arylation of carbonyl compounds - transition-metal catalysis - enantioselective catalysis - aminocatalysis - tertiary stereocentersPublication History
Received: 14 July 2021
Accepted after revision: 28 July 2021
Accepted Manuscript online:
28 July 2021
Article published online:
01 September 2021
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