Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/88490
Title: Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins
Authors: Chen, Xingkuan
Song, Runjiang
Liu, Yingguo
Ooi, Chong Yih
Jin, Zhichao
Zhu, Tingshun
Wang, Hongling
Hao, Lin
Chi, Robin Yonggui
Keywords: Dihydrocoumarins
Enantioselective
Issue Date: 2017
Source: 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.
Series/Report no.: Organic Letters
Abstract: 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.
URI: https://hdl.handle.net/10356/88490
http://hdl.handle.net/10220/44659
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.7b02883
Rights: © 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].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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