Lewis acid-catalyzed regioselective synthesis of chiral alpha-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines

A tunable and highly regio- and diastereoselective addition of acyclic silyl dienolates 2 to several alpha-fluoroalkyl sulfinylimines 1 was developed. By appropriate choice of the Lewis acid catalyst, two new chiral alpha-fluoroalkyl amines 3 and 4 were obtained in good yields and excellent diastere...

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Published inChemical communications (Cambridge, England) Vol. 49; no. 68; pp. 7492 - 7494
Main Authors Liu, Yingle, Liu, Jiawang, Huang, Yangen, Qing, Feng-Ling
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.09.2013
Subjects
Amines
Amines - chemical synthesis
Amines - chemistry
Asymmetry
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Fluorination
Imines - chemistry
Lewis acid
Lewis Acids - chemistry
Molecular Structure
Oxazoles - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Sulfur Compounds - chemistry
Synthesis
ALDIMINES
PHOSPHORIC-ACID
COPPER-MEDIATED DIFLUOROMETHYLATION
EFFICIENT SYNTHESIS
CARBONYL-COMPOUNDS
ARYL
VINYLOGOUS MANNICH REACTIONS
BROMODIFLUOROMETHYLATING REAGENTS
NUCLEOPHILIC DIFLUOROMETHYLATION
DERIVATIVES
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Summary:A tunable and highly regio- and diastereoselective addition of acyclic silyl dienolates 2 to several alpha-fluoroalkyl sulfinylimines 1 was developed. By appropriate choice of the Lewis acid catalyst, two new chiral alpha-fluoroalkyl amines 3 and 4 were obtained in good yields and excellent diastereoselectivities (up to >99 : 1 dr), respectively.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc43741h