Diastereoselective Aldol Reaction of α‐Azido Ketones with α‐CF3 Pyruvate to Organoazides with Vicinal Tetrasubstituted Carbons

A direct diastereoselective aldol reaction of cyclic or acyclic α‐azido ketones with α‐trifluoromethyl (CF3) pyruvate catalysed by DABCO is developed, which allowed the facile access of CF3‐containing multifunctional organoazides with vicinal tetrasubstituted carbons in good to high yields and diast...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 27; no. 26
Main Authors Gao, Yang, Zhang, Xue‐Xin, Tu, Zhi, Yu, Jin‐Sheng, Zhou, Jian
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 08.07.2024
Subjects
Aldehydes
aldol reaction
Enantiomers
Ketones
organocatalysis
Stereoselectivity
Substrates
trifluoromethyl organoazides
vicinal tetrasubstituted carbons
α-azido ketones
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Summary:A direct diastereoselective aldol reaction of cyclic or acyclic α‐azido ketones with α‐trifluoromethyl (CF3) pyruvate catalysed by DABCO is developed, which allowed the facile access of CF3‐containing multifunctional organoazides with vicinal tetrasubstituted carbons in good to high yields and diastereoselectivities. Moreover, phenylethynyl trifluoro‐ and difluoromethyl ketones are also viable substrates. Up to 50 % enantioselectivity could be obtained in the initial exploration of the catalytic asymmetric variant. An organocatalytic direct aldol reaction of α‐azido ketones and α‐trifluoromethyl pyruvate for the diastereoselective synthesis of β‐CF3 organoazides with contiguous tetrasubstituted carbons is described, providing access to valuable multifunctional trifluoromethyl organoazides in good to excellent yields, with moderate diastereoselectivities.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400348