Journal
ACS CATALYSIS
Volume 6, Issue 9, Pages 5747-5763Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b01725
Keywords
aminal; hemiaminal; carbinolamine; acetal; asymmetric catalysis; heterocycles; iminium ion; imine
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Funding
- National Natural Science Foundation of China [21303128, 21573169]
- Fundamental Research Funds for Central Universities [WUT: 2016-IB-007, 2016-YB-007]
- Marie Curie Integration Grant by the European Union [PCIG10-GA-2011-304218]
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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.
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