Abstract / Description of output
N,O-aminals, molecules bearing a geminally N,O -substituted (stereogenic) carbon center, have been recently recognized as an important class of building blocks in organic synthesis. As direct precursors of imines and iminium ions, N,O-aminals were converted through asymmetric organocatalysis or metal catalysis to diverse enantiomerically enriched compounds including N-heterocycles. Furthermore, cyclic N,O-hemiaminals acted as acyclic amino aldehyde surrogates, which were transformed to enantioenriched products otherwise challenging to access. Finally, cyclic N,O-aminals were formed in situ as key intermediates in asymmetric catalysis. In this review, we introduce a wide array of catalytic asymmetric protocols involving the use of four distinct types of N,O-aminals as starting materials or key intermediates.
Original language | English |
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Pages (from-to) | 5747-5763 |
Number of pages | 17 |
Journal | ACS Catalysis |
Volume | 6 |
Issue number | 9 |
Early online date | 15 Jul 2016 |
DOIs | |
Publication status | E-pub ahead of print - 15 Jul 2016 |
Keywords / Materials (for Non-textual outputs)
- aminal
- hemiaminal
- carbinolamine
- acetal
- asymmetric catalysis
- heterocycles
- iminium ion
- imine
- CHIRAL PHOSPHORIC-ACID
- N-ACYLIMINIUM IONS
- FRIEDEL-CRAFTS REACTION
- C-H ACTIVATION
- PALLADIUM(II)-CATALYZED ENANTIOSELECTIVE SYNTHESIS
- ORGANOCATALYTIC TRANSFER HYDROGENATION
- TETRAHYDRO-BETA-CARBOLINES
- BAYLIS-HILLMAN REACTION
- MANNICH-TYPE REACTIONS
- DIELS-ALDER REACTION