Cooperative assistance of a sulfonamide in a proline-mediated direct asymmetric aldol addition

A sulfonamide moiety was introduced at the C-4 position of proline, cis to the -COOH group, to examine a possible intramolecular synergistic interaction between the two functional groups and the consequent influence on the enamine mediated asymmetric aldol reaction. The resultant catalyst was profic...

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Bibliographic Details
Published inNew journal of chemistry Vol. 47; no. 36; pp. 1742 - 175
Main Authors Kumari, Kiran, Bhati, Meeta, Madhukar, Roopendra Singh, Khan, Akram Gulam Hussain, Janjani, Prachi, Rajagopala Reddy, S, Easwar, Srinivasan
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 18.09.2023
Subjects
Adducts
Aldehydes
Asymmetry
Functional groups
Proline
Sulfonamides
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Summary:A sulfonamide moiety was introduced at the C-4 position of proline, cis to the -COOH group, to examine a possible intramolecular synergistic interaction between the two functional groups and the consequent influence on the enamine mediated asymmetric aldol reaction. The resultant catalyst was proficient in furnishing the aldol adducts in commendable yields, along with excellent diastereo- and enantioselectivities in the presence of water. The proposed cooperative assistance was also the subject of a brief computational study to gain a deeper insight. A sulfonamide moiety was introduced at the C-4 position of proline, cis to the -COOH group, to examine a possible synergistic interaction between the two groups and the consequent influence on the enamine mediated asymmetric aldol reaction.
Bibliography:1
Electronic supplementary information (ESI) available: Computational studies on the transition states, transition states for the desymmetrisation reaction, specific rotations of purified aldol adducts, chiral HPLC data of the aldol adducts
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C NMR spectra of the aldol adducts, and
https://doi.org/10.1039/d3nj02685j
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C NMR spectra and HRMS analysis reports of the catalysts and catalyst precursors. See DOI
H and
H NMR spectra of the crude reaction mixtures
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 14
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj02685j