138555-57-4Relevant articles and documents
One-Step Synthesis of ortho-Hydroxycinnamaldehyde
Kim, Jong Han,Lee, Sangku,Kwon, Mu-Gil,Park, Yong Soo,Choi, Sung-Kyu,Kwon, Byoung-Mog
, p. 1223 - 1228 (2004)
An improved and convenient one-step procedure for the large scale synthesis of ortho-hydroxycinnamaldehyde (3a) using ortho-hydroxybenzaldehyde and vinyl acetate is described.
Substrate-Controlled Chemo-/Enantioselective Synthesis of α-Benzylated Enals and Chiral Cyclopropane-Fused 2-Chromanone Derivatives
Byeon, Huimyoung,Ryu, Sunghyeon,Yoo, Eun Jeong,Yang, Jung Woon
supporting information, p. 5085 - 5091 (2021/09/20)
Substrate-controlled cascade reactions between α,β-unsaturated aldehydes or their analogues and 2,4-dinitrobenzyl chloride in the presence of a chiral secondary amine as the catalyst and base were developed, to obtain a broad spectrum of α-benzylated enals and enantioenriched cyclopropane-fused chroman-2-one derivatives. The cyclopropane-tethered iminium ion clearly served as a key intermediate in these reactions to trigger stereochemical outcomes, one of which was supported by a control experiment. (Figure presented.).
Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion
Hayashi, Yujiro,Koshino, Seitaro,Kwon, Eunsang,Monde, Kenji,Taniguchi, Tohru
, p. 15786 - 15794 (2021/10/14)
Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.
