Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 9, Pages 5763-5772Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00728
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Funding
- Synthesis and Solid State Pharmaceutical Centre (SSPC)
- Science Foundation Ireland (SFI) [12/RC/2275]
- SSPC
- Irish Research Council (IRC) [GOIPD/2015/453]
- Higher Education Authority's PRTLI
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A practical application of the UCD-PHIM ligand in the copper-catalyzed asymmetric A3 coupling is reported for aromatic, alkenylic, and alkynylic aldehydes under mild reaction conditions, low catalytic loading, and at ambient temperature. A broad range of aldehydes, secondary amines with a cheaper ethyne equivalent, 2-methyl-3-butyn-2-ol, was explored and enantioselectivities of up to 99% ee were obtained. The importance of (i) axial chirality and central chirality, (ii) imidazoline moiety over oxazoline moiety, and (iii) phosphine unit is investigated for A3 coupling by synthesizing and testing a series of related ligands to UCD-PHIM.
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