18435-82-0Relevant academic research and scientific papers
Preparation method of trans-3, 4-diaryl dihydrocoumarin compound
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Paragraph 0026-0033; 0040-0041, (2021/07/14)
The invention discloses an effective regioselectivity and diastereoselectivity method. A trans-3, 4-diaryl dihydrocoumarin compound is prepared through [4 + 2] cyclization reaction of alkyne amine and o-hydroxybenzyl alcohol under the condition of non-metal catalysis. Alkyne amine is used as a 2-pi partner and reacts with o-hydroxybenzyl alcohol through the positioning effect of sulfonamide, and various trans-3, 4-diaryl dihydrocoumarin compounds are prepared with good yield and high regioselectivity and diastereoselectivity. The non-metal catalytic reaction method has a wide substrate application range and good functional group tolerance, and can be used for efficiently producing in a gram scale.
Regio- And diastereoselective synthesis of: Trans -3,4-diaryldihydrocoumarins via metal-free [4+2] annulation of ynamides with o -hydroxybenzyl alcohols
Luo, Wen-Feng,Ye, Long-Wu,Li, Long,Qian, Peng-Cheng
supporting information, p. 5032 - 5035 (2021/05/28)
An efficient regio- and diastereoselective method for the construction of valuable trans-3,4-diaryldihydrocoumarins via metal-free [4+2] annulation of ynamides with o-hydroxybenzyl alcohols has been developed. Ynamides are first treated as 2-π partners to react with o-hydroxybenzyl alcohols via traceless sulfonamide directing groups, affording trans-3,4-diaryldihydrocoumarins in good yields with high regio- and diastereoselectivities. This metal-free methodology is also characterized by a wide substrate scope, good functional group tolerance, and efficiency on a gram scale.
Phosphoric Acid Catalyzed Aldehyde Addition to in Situ Generated o-Quinone Methides: An Enantio- and Diastereoselective Entry toward cis-3,4-Diaryl Dihydrocoumarins
Spanka, Matthias,Schneider, Christoph
supporting information, p. 4769 - 4772 (2018/08/24)
A highly stereoselective, phosphoric acid catalyzed synthesis of cis-3,4-diarylchromanols through reaction of o-hydroxybenzhydryl alcohols and aryl acetaldehydes is reported. The products can be further manipulated to 3,4-dihydrocoumarins, 4H-chromenes, and chromanes with good overall yields and very good diastereo- and enantiocontrol. This reaction is based upon the concept of enol catalysis and comprises the in situ generation of hydrogen-bonded o-quinone methides and their formal [4 + 2]-cycloaddition with aldehyde enols.
