Tandem Dihydroxylation, Hemiketalization and Conjugate Addition Leading to a Singly Anomeric Spiroketal

Jason A. Davy; Benoît Moreau; Jeremy E. Wulff

doi:10.1055/s-0031-1290817

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(12): 1854-1862
DOI: 10.1055/s-0031-1290817

special topic

Tandem Dihydroxylation, Hemiketalization and Conjugate Addition Leading to a Singly Anomeric Spiroketal

Jason A. Davy

^aDepartment of Chemistry, University of Victoria, Victoria, BC, V8W 3V6, Canada

,

Benoît Moreau

^bBoehringer Ingelheim (Canada) Ltd., Research and Development, 2100 rue Cunard, Laval, QC, H7S 2G5, Canada, Fax: +1(250)7217147 eMail: wulff@uvic.ca

,

Jeremy E. Wulff*

^aDepartment of Chemistry, University of Victoria, Victoria, BC, V8W 3V6, Canada

› Institutsangaben

Abstract

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Abstract

A novel, highly stereoselective tandem dihydroxylation, hemiketalization and conjugate addition reaction is reported that transforms a linear meso-functionalized bis-enone into a substituted singly anomeric spiroketal, effectively controlling six stereocenters in a single operation. As part of an effort to explore the thermodynamic consequences of establishing the singly anomeric spiroketal in this system, the assembly of a related fully anomeric spiroketal possessing an unusual ketal-spiroketal-ketal framework is demonstrated.

Key words

tandem reaction - spiro compounds - dihydroxylation - stereoselective synthesis - enones

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Referenzen

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