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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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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Abstract 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.
AbstractList 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.
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.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.
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.
Author Janiak, Agnieszka
Bardzi ski, Mateusz
Skowronek, Pawe
Prusinowska, Natalia
AuthorAffiliation Department of Chemistry
Adam Mickiewicz University
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  surname: Bardzi ski
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  surname: Janiak
  fullname: Janiak, Agnieszka
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Snippet We have found that derivatization of the trianglamine macrocycle by aliphatic aldehydes leads selectively to one of the two possible diastereomeric aminal...
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SubjectTerms Aldehydes
Chemistry
Chemistry, Organic
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
Stereoselectivity
Symmetry
X ray analysis
Title Symmetry-driven diastereoselective functionalization of simple trianglamine
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