Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins
A highly enantioselective method for quick access to dihydrocoumarins is reported. The reaction involves a cooperative catalytic process with carbene and in situ generated Brønsted acid as the catalysts. α-Chloro aldehyde and readily available and stable o-hydroxybenzhydryl amine substrates were use...
Saved in:
| Main Authors: | , , , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2018
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/88490 http://hdl.handle.net/10220/44659 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| id |
sg-ntu-dr.10356-88490 |
|---|---|
| record_format |
dspace |
| spelling |
sg-ntu-dr.10356-884902023-02-28T19:23:57Z Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins Chen, Xingkuan Song, Runjiang Liu, Yingguo Ooi, Chong Yih Jin, Zhichao Zhu, Tingshun Wang, Hongling Hao, Lin Chi, Robin Yonggui School of Physical and Mathematical Sciences Dihydrocoumarins Enantioselective A highly enantioselective method for quick access to dihydrocoumarins is reported. The reaction involves a cooperative catalytic process with carbene and in situ generated Brønsted acid as the catalysts. α-Chloro aldehyde and readily available and stable o-hydroxybenzhydryl amine substrates were used to generate reactive azolium ester enolate and ortho-quinone methide (o-QM) intermediates, respectively, to form dihydrocoumarins with exceptionally high diastereo- and enantioselectivities. The catalytic reaction products can be easily transformed to valuable pharmaceuticals and bioactive molecules. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2018-04-09T08:03:30Z 2019-12-06T17:04:24Z 2018-04-09T08:03:30Z 2019-12-06T17:04:24Z 2017 2017 Journal Article Chen, X., Song, R., Liu, Y., Ooi, C. Y., Jin, Z., Zhu, T., et al. (2017). Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins. Organic Letters, 19(21), 5892-5895. 1523-7060 https://hdl.handle.net/10356/88490 http://hdl.handle.net/10220/44659 10.1021/acs.orglett.7b02883 205161 en Organic Letters © 2017 American Chemical Society (ACS). This is the author created version of a work that has been peer reviewed and accepted for publication by Organic Letters, American Chemical Society (ACS). It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1021/acs.orglett.7b02883]. 6 p. application/pdf |
| institution |
Nanyang Technological University |
| building |
NTU Library |
| continent |
Asia |
| country |
Singapore Singapore |
| content_provider |
NTU Library |
| collection |
DR-NTU |
| language |
English |
| topic |
Dihydrocoumarins Enantioselective |
| spellingShingle |
Dihydrocoumarins Enantioselective Chen, Xingkuan Song, Runjiang Liu, Yingguo Ooi, Chong Yih Jin, Zhichao Zhu, Tingshun Wang, Hongling Hao, Lin Chi, Robin Yonggui Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins |
| description |
A highly enantioselective method for quick access to dihydrocoumarins is reported. The reaction involves a cooperative catalytic process with carbene and in situ generated Brønsted acid as the catalysts. α-Chloro aldehyde and readily available and stable o-hydroxybenzhydryl amine substrates were used to generate reactive azolium ester enolate and ortho-quinone methide (o-QM) intermediates, respectively, to form dihydrocoumarins with exceptionally high diastereo- and enantioselectivities. The catalytic reaction products can be easily transformed to valuable pharmaceuticals and bioactive molecules. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Chen, Xingkuan Song, Runjiang Liu, Yingguo Ooi, Chong Yih Jin, Zhichao Zhu, Tingshun Wang, Hongling Hao, Lin Chi, Robin Yonggui |
| format |
Article |
| author |
Chen, Xingkuan Song, Runjiang Liu, Yingguo Ooi, Chong Yih Jin, Zhichao Zhu, Tingshun Wang, Hongling Hao, Lin Chi, Robin Yonggui |
| author_sort |
Chen, Xingkuan |
| title |
Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins |
| title_short |
Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins |
| title_full |
Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins |
| title_fullStr |
Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins |
| title_full_unstemmed |
Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins |
| title_sort |
carbene and acid cooperative catalytic reactions of aldehydes and o-hydroxybenzhydryl amines for highly enantioselective access to dihydrocoumarins |
| publishDate |
2018 |
| url |
https://hdl.handle.net/10356/88490 http://hdl.handle.net/10220/44659 |
| _version_ |
1759856397049135104 |