Enantioselective Synthesis of a Hydroxymethyl-cis-1,3-cyclopentenediol Building Block

Enantioselective Synthesis of a Hydroxymethyl-cis-1,3-cyclopentenediol Building Block

A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlig...

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Veröffentlicht in:Organic letters 2012-11, Vol.14 (22), p.5716-5719
Hauptverfasser: Craig, Robert A, Roizen, Jennifer L, Smith, Russell C, Jones, Amanda C, Stoltz, Brian M
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemical synthesis
Alcohols - chemistry
Alkylation
Catalysis
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Dioxanes - chemistry
Molecular Structure
Palladium - chemistry
Stereoisomerism
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Zusammenfassung:A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3027297