Diastereoselective synthesis of a highly substituted cis-decahydroquinoline via a Knoevenagel condensation

Huang, Junfeng; Bergmeier, Stephen C.

doi:10.1016/j.tet.2008.04.073

Cited by 15 publications

(4 citation statements)

References 48 publications

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“…We assembled C 1 -BISPA 2a and C 1 -symmetric monophosphoric acids 3a and 3b to evaluate the importance of two phosphoric acid moieties in the catalytic enantioselective Diels–Alder reactions of α-haloacroleins with N -Cbz amidodiene, considering the synthetic versatility of the resulting adducts and, in addition, the advancement of this methodology (Table ). − Treatment of α-bromoacrolein ( 5a ) (1.5 equiv) with N -Cbz amidodiene 4a (1.0 equiv) in toluene in the presence of 2.5 mol % of 2a at −78 °C for 24 h resulted in the formation of 6aa in 29% yield with 71% ee (1 S ,6 S ) (entry 1). In sharp contrast, the enantioselectivities in the presence of 5 mol % of 3a or 3b dropped significantly (8% ee) under the same conditions (entries 2 and 3).…”

Section: Resultsmentioning

confidence: 99%

Hydrogen Bonds-Enabled Design of a C₁-Symmetric Chiral Brønsted Acid Catalyst

et al. 2016

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We have developed new C 1-symmetric, chiral bis-phosphoric acids with an electron-withdrawing group as one of the two substituents. This C 1-symmetric, chiral bis-phosphoric acid with a pentafluorophenyl group performs exceptionally well in the asymmetric Diels–Alder reaction of acrolein, methacrolein, and α-haloacroleins with substituted amidodienes. Control over the atropisomeric catalyst structure, enhancement of the catalytic activity, and differentiation of the asymmetric reaction space is possible by the remote control of the pentafluorophenyl group. Furthermore, we have conducted theoretical studies to clarify the roles of both intra- and intermolecular hydrogen bonds in the C 1-symmetric chiral environment of chiral bis-phosphoric acid catalysts. The developed strategy, C 1-symmetric catalyst design through hydrogen bonding, is potentially applicable to the development of other chiral Brønsted acid catalysts.

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Section: Resultsmentioning

confidence: 99%

Hydrogen Bonds-Enabled Design of a C₁-Symmetric Chiral Brønsted Acid Catalyst

et al. 2016

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“…The strategy for the synthesis of the BE analogues, represented by compound 5 , is shown in Scheme . During the course of this work the first synthesis of a BE‐ring analogue of methyllycaconitine was reported26 however, no data on this analogue's ability to bind to α7 nAChRs was included. Importantly, this BE analogue did not contain the critical 2‐(2′‐methylsuccinimido)benzoate pharmacophore.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine

et al. 2009

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The synthesis of AE and BE analogues of the alkaloid methyllycaconitine is reported. The analogues contain two key pharmacophores: a 2‐(2‐methylmaleimido)benzoate ester and a homocholine motif formed from a tertiary N‐(3‐phenylpropyl)amine incorporated into either a 3‐azabicyclo[3.3.1]nonane (AE) or octahydroquinoline (BE) ring system. An additional aromatic group is introduced into the AE bicyclic system using a Horner–Wadsworth–Emmons reaction. The BE analogues are synthesised by a one‐pot cyclisation using ethyl α‐(bromomethyl)acrylate, a primary amine and cyclohexanone leading to an efficient assembly of an octahydroquinoline ring system that mimics the BE‐rings of methyllycaconitine. In both the AE and BE analogues, the key 2‐(2‐methylsuccinimido)benzoate ester pharmacophore is introduced by esterification of the alcohol precursors with 2‐(2‐methylmaleimido)benzoic acid (10) under Steglich conditions followed by hydrogenation over palladium on charcoal.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…HRMS was recorded on a commercial apparatus (ESI Source, TOF). Chiral N , N ′-dioxide ligands, ( E )-1-benzyl-4-benzylidenepyrrolidine-2,3-dione, benzyl vinylcarbamate, ethyl vinylcarbamate, and 9 H -fluoren-9-yl vinylcarbamate were prepared according to a previously reported method. − …”

Section: Experimental Sectionmentioning

confidence: 99%

Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes

Zhou

Lü

et al. 2018

J. Org. Chem.

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A highly efficient enantioselective inverse-electron-demand hetero-Diels-Alder reaction of dioxopyrrolidines with heterosubstituted alkenes has been realized by using a N, N'-dioxide/Ni(II) complex as the catalyst. A series of chiral bicyclic dihydropyranes were generated in excellent yields, good dr, and excellent ee values. Besides, a catalytic cycle with a possible transition state was proposed.

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Diastereoselective synthesis of a highly substituted cis-decahydroquinoline via a Knoevenagel condensation

Cited by 15 publications

References 48 publications

Hydrogen Bonds-Enabled Design of a C₁-Symmetric Chiral Brønsted Acid Catalyst

Hydrogen Bonds-Enabled Design of a C₁-Symmetric Chiral Brønsted Acid Catalyst

Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine

Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes

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Diastereoselective synthesis of a highly substituted cis-decahydroquinoline via a Knoevenagel condensation

Cited by 15 publications

References 48 publications

Hydrogen Bonds-Enabled Design of a C1-Symmetric Chiral Brønsted Acid Catalyst

Hydrogen Bonds-Enabled Design of a C1-Symmetric Chiral Brønsted Acid Catalyst

Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine

Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes

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Hydrogen Bonds-Enabled Design of a C₁-Symmetric Chiral Brønsted Acid Catalyst

Hydrogen Bonds-Enabled Design of a C₁-Symmetric Chiral Brønsted Acid Catalyst