A Decade of Advance in the Asymmetric Vinylogous Mannich Reaction

2016/06/21 by María Roselló, María Sánchez‐Roselló, Santos Fustero +1 · 5 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Catalysis #Chemical synthesis and alkaloids #Chemistry #Combinatorial chemistry #Electrophile #Enantioselective synthesis #Ketene #Mannich reaction #Natural product #Organic chemistry #Silylation #Stereochemistry #Synthetic Organic Chemistry Methods #Synthon

paper · doi:10.1055/s-0035-1561650

openalex publication_date 2016/06/21 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/04

Abstract

When the principle of vinylogy is applied to imines as electrophiles, the so-called vinylogous Mannich reaction (VMR), γ-aminocarbonyl (such as butenolides) and β-aminocarbonyl compounds are generated in a very efficient manner. The asymmetric version of this vinylogous Mannich reaction gives access to highly functionalized chiral synthons, which are suitable for further transformations. The versatility of this methodology is exemplified with the synthesis of several alkaloids and natural products. 1 Introduction 2 Asymmetric Vinylogous Mannich Reactions (VMR) with 2-Silyl­oxyfurans and 2-Silyloxypyrroles 3 Asymmetric VMR with Acyclic Silyl Dienolates and Silyl Dienol Ketene Acetals 4 Asymmetric VMR with γ-Butenolides and γ-Butyrolactams 5 Asymmetric VMR with α,α-Dicyanoolefins 6 Miscellaneous Donors in Asymmetric VMR 7 Application of the VMR to Natural Product Synthesis 8 Conclusions

Cited by

• Enantioselective three-component aminomethylation of α-diazo ketones with alcohols and 1,3,5-triazines. [europepmc]
• Computational exploration of copper catalyzed vinylogous aerobic oxidation of unsaturated compounds. [europepmc]
• Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines. [europepmc]
• Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review. [europepmc]
• Total synthesis of the natural (-)-205B alkaloid and its activity toward α7 nAChRs. [europepmc]

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