A Flexible and Stereoselective Synthesis of Azetidin-3-ones through Gold-Catalyzed Intermolecular Oxidation of Alkynes

Chiral rings made easy: Chiral azetidin‐3‐ones have been easily prepared from chiral N‐propargylsulfonamides, which in turn are readily accessible through chiral sulfinamide chemistry (see scheme). Using tert‐butylsulfonyl as the protecting group avoids unnecessary deprotection and reprotection step...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 50; no. 14; pp. 3236 - 3239
Main Authors Ye, Longwu, He, Weimin, Zhang, Liming
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 28.03.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkynes
Alkynes - chemistry
azetidines
Azetidines - chemical synthesis
Azetidines - chemistry
carbenes
Catalysis
Chemistry
Chemistry, Multidisciplinary
cyclization
gold
Gold - chemistry
Molecular Structure
Oxidation-Reduction
Physical Sciences
Science & Technology
Stereoisomerism
stereoselectivity
ASYMMETRIC-SYNTHESIS
ACID
carbenes
cyclization
azetidines
gold
REARRANGEMENT
CYCLOADDITION
stereoselectivity
GLUTAMATE
OXETAN-3-ONES
ALPHA-DIAZO KETONES
EFFICIENT
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Summary:Chiral rings made easy: Chiral azetidin‐3‐ones have been easily prepared from chiral N‐propargylsulfonamides, which in turn are readily accessible through chiral sulfinamide chemistry (see scheme). Using tert‐butylsulfonyl as the protecting group avoids unnecessary deprotection and reprotection steps, and allows its removal from the azetidine ring under acidic conditions.
Bibliography:istex:0AF6311A42F74354DE59804D440251648EDEEF1D
UCSB
NIGMS - No. R01 GM084254
ark:/67375/WNG-QH6QQ2F4-7
ArticleID:ANIE201007624
We thank NIGMS (R01 GM084254) and UCSB for generous financial support and Dr. Guang Wu for assistance with X-ray crystallographic analysis. L.Z. is an Alfred P. Sloan fellow.
We thank NIGMS (R01 GM084254) and UCSB for generous financial support and Dr. Guang Wu for assistance with X‐ray crystallographic analysis. L.Z. is an Alfred P. Sloan fellow.
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201007624