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A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols

1
School of Chemistry and Chemical Engineering, Xuchang University, Xuchang 461000, China
2
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, Henan, China
*
Author to whom correspondence should be addressed.
Academic Editor: Bartolo Gabriele
Molecules 2016, 21(7), 842; https://doi.org/10.3390/molecules21070842
Received: 14 May 2016 / Revised: 21 June 2016 / Accepted: 22 June 2016 / Published: 27 June 2016
(This article belongs to the Special Issue Cascade Catalysis)
Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio- and enantio-selectivity (up to 99% ee). This modular combination, including Jones oxidation and asymmetric organocatalysis, has satisfactory compatibility and reliability even at a 20 mmol scale, albeit without intermediary purification. View Full-Text
Keywords: asymmetric organocatalysis; vinylogous aldol reactions; oxidation; cascade; homoallylic alcohols asymmetric organocatalysis; vinylogous aldol reactions; oxidation; cascade; homoallylic alcohols
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MDPI and ACS Style

Hou, X.; Jing, Z.; Bai, X.; Jiang, Z. A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols. Molecules 2016, 21, 842. https://doi.org/10.3390/molecules21070842

AMA Style

Hou X, Jing Z, Bai X, Jiang Z. A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols. Molecules. 2016; 21(7):842. https://doi.org/10.3390/molecules21070842

Chicago/Turabian Style

Hou, Xufeng, Zhenzhong Jing, Xiangbin Bai, and Zhiyong Jiang. 2016. "A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols" Molecules 21, no. 7: 842. https://doi.org/10.3390/molecules21070842

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