2019
DOI: 10.1016/j.tetlet.2019.03.074
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Asymmetric synthesis of novel spirocycles via a chiral phosphoric acid catalyzed desymmetrization

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Cited by 10 publications
(7 citation statements)
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“…Petersen and co‐workers prepared spirocyclic γ‐lactone‐δ‐lactam 158 from di‐ tert ‐butyl malonate derivative 156 which bears two alkyl chains containing terminal protected nucleophiles, at its α‐carbon (Scheme 47). [63] Molecule 158 was synthesized through a two‐step synthetic pathway in 23% overall yield. The reaction protocol comprises as first step the removal of the benzyl protecting group with 20% Pd(OH) 2 /C.…”
Section: Spiro‐δ‐lactamsmentioning
confidence: 99%
“…Petersen and co‐workers prepared spirocyclic γ‐lactone‐δ‐lactam 158 from di‐ tert ‐butyl malonate derivative 156 which bears two alkyl chains containing terminal protected nucleophiles, at its α‐carbon (Scheme 47). [63] Molecule 158 was synthesized through a two‐step synthetic pathway in 23% overall yield. The reaction protocol comprises as first step the removal of the benzyl protecting group with 20% Pd(OH) 2 /C.…”
Section: Spiro‐δ‐lactamsmentioning
confidence: 99%
“…With their continuous interest on enantioselective desymmetrization of diesters via CPA‐catalyzed intramolecular transesterification reactions, in 2020, Petersen and co‐workers reported the asymmetric synthesis of enantioenriched 1,4‐dioxanones, 1,4‐morpholinones and 3,4‐dihydrocoumarins through this protocol (Scheme 44). [60] In comparing with the formation of the five‐membered lactones in the previous work, the formation of the six‐membered lactone required higher reaction temperature (100 °C). Nevertheless, good to high enantioselectivities were still obtained in these reactions.…”
Section: Chiral Phosphoric Acids Catalyzed Enantioselective Desymmetrizationmentioning
confidence: 81%
“…In first step desymmetrization via a chiral Brønsted acid yielded enantioenriched lactones, which further underwent cyclization to give the desired spirocycles (Scheme 94). [135]…”
Section: Chiral Phosphoric Acid Catalyzed Desymmetrizationmentioning
confidence: 99%
“…Recently, Petersen and coworkers established an efficient strategy for the asymmetric synthesis of lactoneandlactam based spirocycles. In first step desymmetrization via a chiral Brønsted acid yielded enantioenriched lactones, which further underwent cyclization to give the desired spirocycles (Scheme ) …”
Section: Spiro δβγ‐Butenolidesmentioning
confidence: 99%