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...
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| Veröffentlicht in: | Organic letters 2017-11, Vol.19 (21), p.5892-5895 |
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| container_issue | 21 |
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| container_title | Organic letters |
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| creator | Chen, Xingkuan Song, Runjiang Liu, Yingguo Ooi, Chong Yih Jin, Zhichao Zhu, Tingshun Wang, Hongling Hao, Lin Chi, Yonggui Robin |
| 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. |
| doi_str_mv | 10.1021/acs.orglett.7b02883 |
| format | Article |
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| title | Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o‑Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins |
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