Naslov
Asymmetric addition of thiols to in situ generated ketimines

Autori
Suć, Josipa ; Dokli, Irena ; Gredičak, Matija

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, ostalo

Izvornik
6th EuCheMS Symposium - Book of Abstracts, Seville, Spain 11-15. rujan 2016. / - , 2016

Skup
6th EuCheMS Symposium

Mjesto i datum
Sevilla, Španjolska, 11.09.2016. - 15.09.2016

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
organocatalysis, asymmetric addition to ketimines, thiols

Sažetak
N(acyl), S¬-acetals are important structural motifs in many natural products investigated for their sedative, and cell growth and HIV-1 inhibitory properties. They are also present as a key functional group in pharmacologically active compounds, such as β-lactam antibiotics. Enantioselective variants for the synthesis of chiral N(acyl), S-acetals are scarcely known. Major drawbacks of developed protocols are employment of unstable ketimine substrates, with the limitations to acyclic systems that generate products with tertiary stereocenters. Herein we report the first organocatalytic asymmetric addition of thiols to N-Acyl ketimines generated in situ from 3-hydroxy isoindolinones. The reaction proceeds smoothly with a broad range of ketimines and thiols using a chiral Brønsted acid catalyst to afford N(acyl), S-acetals comprising tetrasubstituted stereocenters in excellent yields (up to 98 %) and enantioselectivities (up to 97 % ee). The usefulness of the developed protocol is demonstrated in the synthesis of a known HIV-1 reverse transcriptase inhibitor.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA