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CC BY ND NC 4.0 · Synthesis 2019; 51(01): 1-30
DOI: 10.1055/s-0037-1610386
DOI: 10.1055/s-0037-1610386
review
Palladium-Catalyzed Asymmetric Allylic Alkylation Strategies for the Synthesis of Acyclic Tetrasubstituted Stereocenters
Funding was provided in part by the Tamaki Foundation.Further Information
Publication History
Received: 23 October 2018
Accepted: 24 October 2018
Publication Date:
05 December 2018 (online)
Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue
Abstract
Over the past 20 years, the asymmetric synthesis of acyclic tetrasubstituted stereocenters by Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) strategies has seen considerable growth. Despite the inherent difficulty in accessing acyclic tetrasubstituted stereocenters, creative approaches toward this problem have resulted in high stereoinduction on both electrophilic and nucleophilic reaction partners. Much of this chemistry has paved the way for unique solutions in Mo-, Ir-, and Rh-AAA, with many complimentary methods arising due to the unique regiochemical outcomes of AAA outside of Pd catalysis.
1 Introduction
2 Stereocontrol on Prochiral Electrophiles
3 Stereocontrol on Prochiral Nucleophiles
4 Temporary Cyclic Pronucleophiles
5 Allylic Alkylation with Other Metals
6 Conclusions and Outlook
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