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 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.

Automated summary

A sulfonamide moiety was introduced at the C-4 position of proline, cis to the -COOH group, to investigate the potential synergistic interaction between the two functional groups and its influence on the enamine mediated asymmetric aldol reaction. The resulting catalyst exhibited high efficiency in producing aldol adducts with excellent diastereo- and enantioselectivities in the presence of water. Computational study was also conducted to gain further insights into the proposed cooperative assistance.