Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions

Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yield (up to 98%) with high to excellent enanti...

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Published inOrganic letters Vol. 21; no. 17; pp. 6679 - 6683
Main Authors Kang, Ki-Tae, Park, Sang Hyun, Ryu, Do Hyun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.09.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BRONSTED ACID
MANNICH REACTION
KETONES
C-H BOND
DIELS-ALDER REACTIONS
LEWIS-ACID
CYCLOADDITIONS
ASYMMETRIC ROSKAMP REACTION
ALDEHYDES
DIAZOESTERS
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Summary:Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yield (up to 98%) with high to excellent enantioselectivity (up to 99% ee). A rational mechanistic model for the complex of COBI and aldimine is provided to account for these enantioselective reactions.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02280