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DOI: 10.1055/s-0040-1707207
Unconventional Transformations of Morita–Baylis–Hillman Adducts
This work was supported by the University of Padova and the GREEN C-C Supporting TAlent in ReSearch (STARS) starting grant (XC).Publication History
Received: 17 May 2020
Accepted after revision: 15 June 2020
Publication Date:
29 July 2020 (online)
![](https://www.thieme-connect.de/media/synthesis/202020/lookinside/thumbnails/ss-2020-m0271-sr_10-1055_s-0040-1707207-1.jpg)
Dedicated to Professor Albert Moyano on the occasion of his 65th birthday
Abstract
Morita–Baylis–Hillman (MBH) adducts are versatile starting materials widely employed in Lewis base catalysis. A myriad of different transformations have been reported based on either allylic alkylations with stabilised nucleophiles or annulations with diverse dipolarophiles. Apart from these two conventional types of reactivity, MBH adducts have recently been implemented in alternative and complementary catalytic strategies, including: (i) one-pot and cascade transformations, where additional chemical bonds are formed following the asymmetric allylic alkylation event in a single synthetic operation; (ii) regioselective α-allylations for the synthesis of trisubstituted alkenes; and (iii) dual activation strategies, involving Lewis base catalysis together with transition metal complexes or light, enabling allylic alkylations with nonstabilised nucleophiles and cascade processes. The present Short Review summarises the most significant unconventional catalytic transformations of racemic MBH adducts reported within the last decade.
1 Introduction
2 Multi-Step Single-Vessel Transformations (path iii)
2.1 One-Pot Transformations
2.2 Cascade Transformations
3 α-Allylations (path iv)
3.1 SN2′ Mechanism
3.2 SN2′–SN2 Mechanism
3.3 Miscellaneous Mechanisms
4 Dual Activation (path v)
4.1 MBH Adduct as Electrophile
4.2 MBH Adduct as Nucleophile
5 Summary and Outlook
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61 This Short Review was written in April 2020 during the worldwide lockdown caused by the SARS-CoV-2 pandemic outbreak.
For selected examples, see:
For selected examples, see:
For selected examples, see:
For selected examples, see:
For authoritative reviews, see:
For examples of non-catalytic α-allylation of MBH carbonates, see:
For the phase-transfer-catalysed α-allylation of glycine derivatives with MBH acetates, see:
For the corresponding Cu- and Ag-catalysed transformations, see: