z-logo
Premium
Homochiral bifunctional L ‐prolinamide‐ and L‐ bis‐prolinamide‐catalyzed asymmetric aldol reactions performed in wet solvent‐free conditions
Author(s) -
Huelgas Gabriela,
Somanathan Ratnasamy,
Hernández Pérez Julio M.,
Rojas Cabrera Haydee,
Higuera Macías Maximiliano,
DomínguezHuerta Alejandra,
Sabala Rocío,
Anaya de Parrodi Cecilia
Publication year - 2021
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23283
Subject(s) - chemistry , bifunctional , enantioselective synthesis , aldol reaction , enantiomer , enantiomeric excess , thiourea , intermolecular force , solvent , catalysis , asymmetric induction , organocatalysis , organic chemistry , medicinal chemistry , stereochemistry , molecule
In this study, the novel bifunctional homochiral thiourea‐ L ‐prolinamides 1–4 , tertiary amino ‐L ‐prolinamide 5 , and bis‐ L ‐prolinamides 6 and 7 were prepared from enantiomerically pure (11 R ,12 R )‐11,12‐diamino‐9,10‐dihydro‐9,10‐ethanoanthracene 8 and (11 S ,12 S )‐11,12‐diamino‐9,10‐dihydro‐9,10‐ethanoanthracene ent ‐8 . Highly enantioselective and diastereoselective aldolic intermolecular reactions (up to 95% enantiomeric excess , 93:7 anti / syn ) between aliphatic ketones (20 equiv) and a range of aromatic aldehydes (1 equiv) were successfully carried out in the presence of water (10 equiv) and monochloroacetic acid (10 mol%), solvent‐free conditions, at room temperature over 24 h using organocatalysts 1–7 (5 mol%). Stereoselective induction using density functional theory–based methods was consistent with the experimental data.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here