dc.contributor.author |
Kumar, Indresh |
|
dc.date.accessioned |
2021-10-27T04:27:16Z |
|
dc.date.available |
2021-10-27T04:27:16Z |
|
dc.date.issued |
2019-09-05 |
|
dc.identifier.uri |
https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b01865 |
|
dc.identifier.uri |
http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3160 |
|
dc.description.abstract |
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. |
en_US |
dc.language.iso |
en |
en_US |
dc.publisher |
ACS |
en_US |
dc.subject |
Chemistry |
en_US |
dc.subject |
High-performance liquid chromatography |
en_US |
dc.subject |
Solution chemistry |
en_US |
dc.subject |
Stereoselectivity |
en_US |
dc.subject |
Chemical reactions |
en_US |
dc.title |
Enantio- and Diastereoselective Two-Pot Synthesis of Isoquinuclidines from Glutaraldehyde and N-Aryl Imines with DFT Calculations |
en_US |
dc.type |
Article |
en_US |