Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions
An NHC-catalyzed cascade cycloaddition reaction is developed for quick access to structurally sophisticated tetrahydrochromeno[4,3-b]pyrrole derivatives. A sterically congested tetrasubstituted chirality carbon center is formed during the cyclization process. All the α-, β-, and carbonyl carbons of...
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sg-ntu-dr.10356-1379002023-02-28T19:47:42Z Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions Li, Tingting Wang, Jilan Xu, Jun Jin, Jiamiao Chi, Robin Yonggui Jin, Zhichao School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Chirality N-Hetereocyclic Carbene An NHC-catalyzed cascade cycloaddition reaction is developed for quick access to structurally sophisticated tetrahydrochromeno[4,3-b]pyrrole derivatives. A sterically congested tetrasubstituted chirality carbon center is formed during the cyclization process. All the α-, β-, and carbonyl carbons of the enal substrates are functionalized in chemo- and stereoselective fashion. The multicyclic chromeno[4,3-b]pyrrole products are generally afforded in good yields with excellent enantio- and diastereoselectivities. Heavily substituted pyrroline derivatives can be afforded from the chiral products through simple protocols. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-17T08:52:02Z 2020-04-17T08:52:02Z 2019 Journal Article Li, T., Wang, J., Xu, J., Jin, J., Chi, R. Y., & Jin, Z. (2020). Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions. Organic Letters, 22(1), 326-330. doi:10.1021/acs.orglett.9b04371 1523-7060 https://hdl.handle.net/10356/137900 10.1021/acs.orglett.9b04371 31833772 2-s2.0-85076889978 1 22 326 330 en Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b04371 application/pdf |
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Science::Chemistry::Organic chemistry Chirality N-Hetereocyclic Carbene Li, Tingting Wang, Jilan Xu, Jun Jin, Jiamiao Chi, Robin Yonggui Jin, Zhichao Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions |
| description |
An NHC-catalyzed cascade cycloaddition reaction is developed for quick access to structurally sophisticated tetrahydrochromeno[4,3-b]pyrrole derivatives. A sterically congested tetrasubstituted chirality carbon center is formed during the cyclization process. All the α-, β-, and carbonyl carbons of the enal substrates are functionalized in chemo- and stereoselective fashion. The multicyclic chromeno[4,3-b]pyrrole products are generally afforded in good yields with excellent enantio- and diastereoselectivities. Heavily substituted pyrroline derivatives can be afforded from the chiral products through simple protocols. |
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School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Li, Tingting Wang, Jilan Xu, Jun Jin, Jiamiao Chi, Robin Yonggui Jin, Zhichao |
| format |
Article |
| author |
Li, Tingting Wang, Jilan Xu, Jun Jin, Jiamiao Chi, Robin Yonggui Jin, Zhichao |
| author_sort |
Li, Tingting |
| title |
Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions |
| title_short |
Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions |
| title_full |
Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions |
| title_fullStr |
Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions |
| title_full_unstemmed |
Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions |
| title_sort |
enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/137900 |
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1759854327433789440 |