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Enantio- and diastereoselective double Mannich reaction of malononitrile with N-Boc imines using quinine-derived bifunctional organoiodine catalyst.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2021 Aug 28; Vol. 19 (32), pp. 6969-6973. Date of Electronic Publication: 2021 Aug 02. - Publication Year :
- 2021
-
Abstract
- A chiral quinine-derived organic base catalyst with halogen bond donor functionality was used to catalyze the asymmetric double Mannich reaction of malononitrile with N-Boc and N-Cbz imines to afford 1,3-diamines in excellent yields with high enantio- and diastereoselectivities. With 2.2 equiv. of a single imine electrophile, symmetrical 1,3-diamines were obtained, whereas, with two different imine partners, unsymmetrically substituted 1,3-diamine was obtained. The monohydration of the double Mannich product was also achieved.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 19
- Issue :
- 32
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 34337640
- Full Text :
- https://doi.org/10.1039/d1ob00796c