2020
DOI: 10.1248/cpb.c19-00900
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Organocatalytic Synthesis of Highly Functionalized Heterocycles by Enantioselective aza-Morita–Baylis–Hillman-Type Domino Reactions

Abstract: Organocatalytic enantioselective domino reactions are an extremely attractive methodology, as their use enables the construction of complex chiral skeletons from readily available starting materials in two or more steps by a single operation under mild reaction conditions. Thus, these reactions can save both the quantity of chemicals and length of time typically required for the isolation and/or purification of synthetic intermediates. Additionally, no metal contamination of the products occurs, given that org… Show more

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Cited by 11 publications
(3 citation statements)
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References 104 publications
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“… 15 Several reviews subsequently appeared that focused on the biocatalytic asymmetric MBH reaction, 16 application of DABCO as a catalyst for the MBH reaction, 17 and an organocatalytic MBH-type domino reaction. 18 Because of the wide importance and applicability of this reaction, we have summarized the recent advancements in the organocatalytic MBH reaction, from 2018 to 2023. For additional clarity, this review has been organized based on the organocatalyst utilized.…”
Section: Introductionmentioning
confidence: 99%
“… 15 Several reviews subsequently appeared that focused on the biocatalytic asymmetric MBH reaction, 16 application of DABCO as a catalyst for the MBH reaction, 17 and an organocatalytic MBH-type domino reaction. 18 Because of the wide importance and applicability of this reaction, we have summarized the recent advancements in the organocatalytic MBH reaction, from 2018 to 2023. For additional clarity, this review has been organized based on the organocatalyst utilized.…”
Section: Introductionmentioning
confidence: 99%
“…Here, an alkynyl ester is employed, and the resulting zwitterionic species can react with nucleophiles or electrophiles to afford structurally diverse products. 19 As part of our continuous effort to develop Lewis-base-mediated reactions, 22,23 we envisioned that by using water as both a nucleophile and an electrophile, phosphonium intermediate I and a hydroxide ion would be generated in situ (Scheme 1C). Owing to the high oxophilicity of the phosphonium and neighboring α,β-unsaturated carbonyl moiety (a Michael acceptor) in intermediate I, the hydroxide ion could attack the phosphonium, and, thus, C(aryl)-P bond cleavage would be enhanced and induce the 1,2-rearrangement of the aryl group to the Michael acceptor via a hydroxyl-λ 5 -phosphane 24 intermediate II (Scheme 1C, path a), thus providing 3-(diarylphosphoryl)-3-aryl propanoic acid derivatives.…”
Section: Introductionmentioning
confidence: 99%
“…It involves a reaction of C-C bond formation between sp 2 carbons of an aldehyde as well as an electron-deficient unsaturated hydrocarbon. Under specific reaction conditions, and by using nucleophilic amines or phosphines as catalysts, a powerful multifunctional adduct is achieved [ 6 , 7 ]. Moreover, in the presence of more than one similar position, C-C bond construction at the selective site of the requisite compound is another major challenge for chemists [ 8 ].…”
Section: Introductionmentioning
confidence: 99%