One-Pot Catalytic Asymmetric Synthesis of Pyranones

Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (−)-MIB generates enantioenriched furyl z...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 11; no. 12; pp. 2703 - 2706
Main Authors Cheng, Kevin, Kelly, Ann Rowley, Kohn, Rachel A, Dweck, Jessica F, Walsh, Patrick J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.06.2009
Amer Chemical Soc
Subjects
Alkylation
Catalysis
Chemistry
Chemistry, Organic
Furaldehyde - chemistry
Furans - chemistry
Molecular Structure
Physical Sciences
Pyrones - chemical synthesis
Pyrones - chemistry
Science & Technology
Stereoisomerism
Zinc - chemistry
KETONES
CONCISE
8A-EPI-SWAINSONINE
EPOXY ALCOHOLS
FURANS
DE-NOVO SYNTHESIS
KINETIC RESOLUTION
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
GLYCOSYLATION REACTION
Online AccessGet full text

Cover

More Information
Summary:Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (−)-MIB generates enantioenriched furyl zinc alkoxides. Addition of water/THF followed by NBS results in formation of pyranones with ee’s >90% and yields between 46−77%.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900905r