[3 + 2] Cycloaddition on Carbohydrate Templates: Stereoselective Synthesis of Pyrrolidines

Pyrrolidine derivatives were prepared in high diastereoselectivities and good yields via a [3 + 2] cycloaddition of a tert-butyldimethylsilyl protected carbohydrate-based allene with a diverse range of imines. The subsequent removal of the carbohydrate auxiliary afforded a variety of pyrrolidines wi...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 5; pp. 1072 - 1075
Main Authors Cai, Shuting, Kishan Gorityala, Bala, Ma, Jimei, Leow, Min Li, Liu, Xue-Wei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.03.2011
Amer Chemical Soc
Subjects
Carbohydrates - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Oxidation-Reduction
Physical Sciences
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Science & Technology
Silanes - chemistry
Stereoisomerism
ASYMMETRIC-SYNTHESIS
ACID
DIASTEREOSELECTIVE SYNTHESIS
ANALOGS
ETHER NAZAROV CYCLIZATION
CHIRAL AUXILIARIES
INHIBITORS
CATALYST
DERIVATIVES
HETEROCYCLIC-COMPOUNDS
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Summary:Pyrrolidine derivatives were prepared in high diastereoselectivities and good yields via a [3 + 2] cycloaddition of a tert-butyldimethylsilyl protected carbohydrate-based allene with a diverse range of imines. The subsequent removal of the carbohydrate auxiliary afforded a variety of pyrrolidines with excellent enantioselectivities (up to 99% ee). Selective reduction of the pyrrolidines further demonstrated the potential of this strategy.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol103119u