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Synthesis 2022; 54(04): 887-909
DOI: 10.1055/a-1514-1049
DOI: 10.1055/a-1514-1049
special topic
Cycloadditions – Established and Novel Trends – in Celebration of the 70th Anniversary of the Nobel Prize Awarded to Otto Diels and Kurt Alder
Organocatalyzed Oxa-Diels–Alder Reactions: Recent Progress
M.S.M. gratefully acknowledge the Science & Engineering Research Board (SERB), Department of Science and Technology, New Delhi, India (Sanction No. CRG/2018/000317) for funding. S.K. thanks the University Grants Commission (UGC), India for a fellowship.
Abstract
The oxa-Diels–Alder reaction is a straightforward, atom-economical process for the construction of six-membered oxacycles, which are privileged structures due to their very common occurrence in several pharmaceuticals and natural products. As with many other asymmetric transformations, organocatalysis provides an elegant pathway to their synthesis via [4+2] annulation under mild reaction conditions. The oxa-Diels–Alder reaction utilizes either an α,β-unsaturated carbonyl as an oxa-diene with a suitable dienophile or a simple carbonyl as a dienophile with other dienes. A range of organocatalysts has been explored in the past decade to execute this strategy. The catalysts induce stereoselectivities via two basic reactivities: (1) The formation of chiral intermediates, or (2) selectively activating suitable reactants via a transition state. The present short review compiles organocatalyzed asymmetric oxa-Diels–Alder reactions published over the last ten years, along with detailed discussions on mechanistic approaches.
1 Introduction
2 Catalysis through Covalent Activation
2.1 N-Heterocyclic Carbenes
2.2 Amines
2.3 Isothiourea Catalysis
2.4 Phosphines
3 Catalysis through Non-Covalent Activation
3.1 Bifunctional Amines
3.2 Brønsted Acids
3.3 Guanidines
4 Multicatalysis through Both Covalent and Non-Covalent Activation
5 Conclusion
Publication History
Received: 17 April 2021
Accepted after revision: 20 May 2021
Accepted Manuscript online:
20 May 2021
Article published online:
13 July 2021
© 2021. Thieme. All rights reserved
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