Mala, Zaneta A’s team published research in ChemCatChem in 2021-01-15 | 112-63-0

ChemCatChem published new progress about Aldol addition, stereoselective (intramol.). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Application of C19H34O2.

Mala, Zaneta A.; Janicki, Mikolaj J.; Niedzwiecka, Natalia H.; Gora, Robert W.; Konieczny, Krzysztof A.; Kowalczyk, Rafal published the artcile< Stereoselectivity Enhancement During the Generation of Three Contiguous Stereocenters in Tetrahydrothiophenes>, Application of C19H34O2, the main research area is enantioselective diastereoselective sulfa Michael intramol aldol cascade mercaptoacetaldehyde enynone; thiophene tetrahydro enantioselective diastereoselective synthesis.

Application of carefully designed Cinchona alkaloid based squaramides resulted in the formation of three contiguous stereocenters in enantio- and diastereoselective Sulfa-Michael/intramol. aldol reactions cascade [e.g., I + II → III (62%, 96% ee, 20:1 d.r.)]. Increase of the temperature to 333 K in reaction of mercaptoacetic aldehyde and various en-ynones allowed the rise of the reaction rate while not affecting the enantioselectivity nor diastereoselectivity. Stereoselectivity was dependent on the structure of the hydrogen-bonding unit, thus revealing the importance of weak interactions in the formation of the multifunctional tetrahydrothiophenes. Kohn-Sham D. Functional Theory results suggest that a perfect fit of the electrophile and squaramide via tailored (+)N-H hydrogen bonding and π-π stacking interactions were the main factors of the chirality transfer.

ChemCatChem published new progress about Aldol addition, stereoselective (intramol.). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Application of C19H34O2.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics