Diastereoselective Mukaiyama and Free Radical Processes for the Synthesis of Polypropionate Units

Reported herein is the synthesis of 8 out of 16 polypropionates derived from our propionate units. A new strategy involving a stereoselective Mukaiyama aldol reaction followed by a stereoselective free-radical-based hydrogen transfer, both under Lewis acid control, is used. Of particular interest is...

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 15; pp. 2599 - 2602
Main Authors Guindon, Yvan, Brazeau, Jean-François
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.07.2004
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYDROGEN-TRANSFER REACTIONS
REDUCTION
STEREOCONTROL
ENHANCE STEREOSELECTIVITY
ACYCLIC RADICALS
ADDITION-REACTIONS
IN-SITU DERIVATIZATION
ALDOL REACTIONS
CHELATION
PROPIONATE MOTIFS
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Summary:Reported herein is the synthesis of 8 out of 16 polypropionates derived from our propionate units. A new strategy involving a stereoselective Mukaiyama aldol reaction followed by a stereoselective free-radical-based hydrogen transfer, both under Lewis acid control, is used. Of particular interest is the remarkable reactivity of (i-PrO)TiCl3 in this context to give only the 3,4-anti bromoesters.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol049086h