Enantioselective All-Carbon (4+2) Annulation by N‑Heterocyclic Carbene Catalysis

Enantioselective All-Carbon (4+2) Annulation by N‑Heterocyclic Carbene Catalysis

The enantioselective vinylogous Michael/aldol cascade is an underdeveloped approach to cyclohexenes. Herein we describe a highly enantioselective (most ≥98:2 er) and diastereoselective (all ≥15:1 dr) N-heterocyclic carbene catalyzed cycloisomerization of acyclic dienyl esters to cyclohexyl β-lactone...

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Veröffentlicht in:Journal of the American Chemical Society 2014-10, Vol.136 (41), p.14397-14400
Hauptverfasser: Candish, Lisa, Levens, Alison, Lupton, David W
Format: Artikel
Sprache:eng
Schlagworte:
Carbon - chemistry
Catalysis
Cyclization
Cyclohexenes - chemical synthesis
Cyclohexenes - chemistry
Heterocyclic Compounds - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:The enantioselective vinylogous Michael/aldol cascade is an underdeveloped approach to cyclohexenes. Herein we describe a highly enantioselective (most ≥98:2 er) and diastereoselective (all ≥15:1 dr) N-heterocyclic carbene catalyzed cycloisomerization of acyclic dienyl esters to cyclohexyl β-lactones. Derivatizations avail cyclohexenes bearing four contiguous stereogenic centers, while mechanistic studies support olefin isomerization prior to cyclization.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja508542n