A convenient method for the preparation of 1-olefins by the palladium catalyzed hydrogenolysis of allylic acetates and allylic phenyl ethers with ammonium formate

Tsuji, Jiro; Yamakawa, Tomio

doi:10.1016/s0040-4039(01)86016-0

Cited by 131 publications

(38 citation statements)

References 6 publications

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“…This compound bears anew quaternary carbon center (> 19:1 dr), whose installation is directed by the adjacent stereocenter. Employing reductive conditions with HCOONH 4 [17] delivered ester (+ +)-10 in 77 %y ield with moderate diaste-Scheme 2. Synthesis of benzazepinone(À)-5a and an unexpected indoline (+ +)-5a' '.…”

Section: Angewandte Chemiementioning

confidence: 99%

Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts

Kang

Yamagami²,

Vellalath

et al. 2018

Angew Chem Int Ed

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Medium-sized lactams are important structural motifs found in a variety of bioactive compounds and natural products but are challenging to prepare, especially in optically active form. A Michael addition/proton transfer/lactamization organocascade process is described that delivers medium-sized lactams, including azepanones, benzazepinones, azocanones, and benzazocinones, in high enantiopurity through the intermediacy of chiral α,β-unsaturated acylammonium salts. An unexpected indoline synthesis was also uncovered, and the benzazocinone skeleton was transformed into other complex heterocyclic derivatives, including spiroglutarimides, isoquinolinones, and δ-lactones.

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Section: Angewandte Chemiementioning

confidence: 99%

Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts

Kang

Yamagami²,

Vellalath

et al. 2018

Angew Chem Int Ed

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“…This compound bears a new quaternary carbon center (>19:1 dr), whose installation is directed by the adjacent stereocenter. Employing reductive conditions with HCOONH 4 delivered ester (+)‐ 10 in 77 % yield with moderate diastereoselectivity (4:1 dr). The relative stereochemistry of the major diastereomer was confirmed as anti by X‐ray analysis (Scheme ).…”

Section: Figurementioning

confidence: 99%

Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts

Kang

Yamagami²,

Vellalath

et al. 2018

Angewandte Chemie

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Medium‐sized lactams are important structural motifs found in a variety of bioactive compounds and natural products but are challenging to prepare, especially in optically active form. A Michael addition/proton transfer/lactamization organocascade process is described that delivers medium‐sized lactams, including azepanones, benzazepinones, azocanones, and benzazocinones, in high enantiopurity through the intermediacy of chiral α,β‐unsaturated acylammonium salts. An unexpected indoline synthesis was also uncovered, and the benzazocinone skeleton was transformed into other complex heterocyclic derivatives, including spiroglutarimides, isoquinolinones, and δ‐lactones.

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“…TBS protection of the newly formed hydroxy group, reductive removal of the Evans auxiliary, oxidation of the resulting primary alcohol, and addition of 2-propenylmagnesium bromide to the ensuing aldehyde furnished intermediate 58 . The secondary hydroxy group was acetylated and the acetate was reduced by palladium-catalyzed transfer hydrogenolysis according to a modification of the Tsuji protocol [ 165 ]. Selective cleavage of the primary TPDPS group in the presence of a secondary TBS ether was readily achieved with NaOH in refluxing methanol.…”

Section: Reviewmentioning

confidence: 99%

The chemistry and biology of mycolactones

Gehringer¹,

Altmann²

2017

Beilstein J. Org. Chem.

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Mycolactones are a group of macrolides excreted by the human pathogen Mycobacterium ulcerans, which exhibit cytotoxic, immunosuppressive and analgesic properties. As the virulence factor of M. ulcerans, mycolactones are central to the pathogenesis of the neglected disease Buruli ulcer, a chronic and debilitating medical condition characterized by necrotic skin ulcers. Due to their complex structure and fascinating biology, mycolactones have inspired various total synthesis endeavors and structure–activity relationship studies. Although this review intends to cover all synthesis efforts in the field, special emphasis is given to the comparison of conceptually different approaches and to the discussion of more recent contributions. Furthermore, a detailed discussion of molecular targets and structure–activity relationships is provided.

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A convenient method for the preparation of 1-olefins by the palladium catalyzed hydrogenolysis of allylic acetates and allylic phenyl ethers with ammonium formate

Cited by 131 publications

References 6 publications

Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts

Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts

Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts

The chemistry and biology of mycolactones

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