Stereoselective synthesis of 2,5-disubstituted pyrrolidines via gold-catalysed anti-Markovnikov hydroamination-initiated tandem reactions

A series of gold-catalysed intramolecular anti-Markovnikov hydroamination-initiated azidation, allylation and heteroarylation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 2,5-disubstituted pyrrolidines are obtained in moderate to excellent yields with e...

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Published inChemical communications (Cambridge, England) Vol. 55; no. 67; pp. 9923 - 9926
Main Authors Tan, Tong-De, Chen, Yang-Bo, Yang, Ming-Yang, Wang, Jia-Le, Su, Hao-Ze, Hong, Feng-Lin, Zhou, Jin-Mei, Ye, Long-Wu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 15.08.2019
Royal Society of Chemistry
Subjects
Allyl compounds
allylation
Cascade chemical reactions
catalytic activity
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Crystallography
diastereoselectivity
enantioselectivity
Gold
Physical Sciences
pyrrolidines
Science & Technology
stereoselective synthesis
Stereoselectivity
Sulfonamides
FUNCTIONALIZATION
INTERMOLECULAR REACTION
CHIRAL HOMOPROPARGYL SULFONAMIDES
EFFICIENT SYNTHESIS
CASCADE SYNTHESIS
TERMINAL ALKYNES
RAPID ACCESS
CYCLOISOMERIZATION
OXIDATIVE CYCLIZATION
HIGHLY EFFICIENT
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Summary:A series of gold-catalysed intramolecular anti-Markovnikov hydroamination-initiated azidation, allylation and heteroarylation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 2,5-disubstituted pyrrolidines are obtained in moderate to excellent yields with excellent enantioselectivities and generally high diastereoselectivities.
Bibliography:ObjectType-Article-1
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/C9CC05295J