Symmetry-driven diastereoselective functionalization of simple trianglamine

We have found that derivatization of the trianglamine macrocycle by aliphatic aldehydes leads selectively to one of the two possible diastereomeric aminal products. X-ray analysis, NMR measurements and DFT calculations pointed to the product possessing a higher symmetry. A trianglamine macrocycle ca...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 2; no. 36; pp. 7216 - 722
Main Authors Skowronek, Pawe, Prusinowska, Natalia, Bardzi ski, Mateusz, Janiak, Agnieszka
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.09.2022
Royal Society of Chemistry
Subjects
Aldehydes
Chemistry
Chemistry, Organic
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
Stereoselectivity
Symmetry
X ray analysis
CAGE
ENTROPY
Online AccessGet full text
ISSN1477-0520
1477-0539
1477-0539
DOI10.1039/d2ob01226j

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Summary:We have found that derivatization of the trianglamine macrocycle by aliphatic aldehydes leads selectively to one of the two possible diastereomeric aminal products. X-ray analysis, NMR measurements and DFT calculations pointed to the product possessing a higher symmetry. A trianglamine macrocycle can be easily derivatized by aliphatic aldehydes. Of the two possible diastereomeric aminal products, only one is obtained in good yield.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
https://doi.org/10.1039/d2ob01226j
2184538-2184540
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d2ob01226j