Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 19, Pages 12408-12419Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01865
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Funding
- DST-SERB [EMR/2016/005599]
- OPERA-grant of BITS Pilani
- DST-FIST [SR/FST/CSI-270/2015]
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A pot-economic method for the enantio- and diastereoselective synthesis of a [2.2.2] azabicyclic isoquinuclidine system is developed. This protocol involves the proline-catalyzed direct Mannich reaction-cyclization/IBX-mediated site-selective oxidation/NaBH4-reduction sequence between glutaraldehyde and imines to generate in situ chiral 1,2-DHPs, followed by the diastereoselective Diels-Alder reaction with N-aryl maleimides furnishing isoquinuclidines in overall five steps. A variety of isoquinuclidines having five-contiguous chiral centers, including an all-carbon quaternary, were prepared with high yields (up to 78%) and excellent stereoselectivity (>50:1 dr, and up to >99:1 er). DFT calculations support the observed high stereoselective reaction outcome.
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