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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.