An Efficient Stereoselective Synthesis of Fluorinated Trisubstituted Alkenes

Kawasaki, Tomoko; Ichige, Tatsuro; Kitazume, Tomoya

doi:10.1021/jo9807159

Cited by 30 publications

(12 citation statements)

References 29 publications

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“…A very efficient 2-fluoroacrylate ester synthesis is based on a domino reaction where the first step is the addition of fluoromalonate to an -unsaturated ketone followed by elimination to give a fluoroacrylate derivative. 44 Although the yields vary from poor to excellent, the E/Z selectivity of the reaction is very good (Scheme 11). SCHEME 11.…”

Section: Reactions With Carbon Electrophilesmentioning

confidence: 99%

2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences

Harsányi

Sandford

2014

Org. Process Res. Dev.

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Section: Reactions With Carbon Electrophilesmentioning

confidence: 99%

2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences

Harsányi

Sandford

2014

Org. Process Res. Dev.

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“…Therefore, new stereoselective methods for generating trisubstituted olefins remains an ongoing challenge in the area of synthetic organic chemistry. A wide variety of methods have been investigated to date including intramolecular Claisen rearrangments, , Wittig olefination, Julia couplings, Peterson olefination, alkylation of sulfonyl hydrazones, and direct methods for the preparation of flourinated trisubstituted alkenes . Transition metal mediated routes including hydromagnesization, hydrozirconation, and the use of organocuprates have also been reported but often suffer from use of harsh stoichiometric reagents.…”

mentioning

confidence: 99%

Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis

1999

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“…− MS (EI); m / z (%): 165 (100) [M + − t Bu] [found (HRMS, FAB) for [M + ] 182.1665, C 12 H 22 O requires 182.1671]. − Compound 5c has been described in the literature25,26 but no spectroscopic or physical data were reported 27…”

Section: Methodsmentioning

confidence: 99%

Copper-Catalysed Asymmetric 1,4-Addition of Organozinc Compounds to Linear Aliphatic Enones Using 2,2′-Dihydroxy 3,3′-Dithioether Derivatives of 1,1′-Binaphthalene

et al. 2001

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Directed ortho dilithiation of bis(diethylcarbamate) or bis-(MOM)-protected (S a )-1,1Ј-bi(2-naphthol) followed by treatment with R 2 S 2 [R = Me, Ph (X-ray structure)] or Me 2 Se 2 cleanly affords the 3,3Ј derivatives; the free naphthols are produced on deprotection. In the case of the bis(MOM) series, but not that of the bis(carbamates), some racemisation occurs. The ligand 2,2Ј-dihydroxy-3,3Ј-dimethylthio-1,1Ј-binaphthalene shows optimal performance in the addition of

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An Efficient Stereoselective Synthesis of Fluorinated Trisubstituted Alkenes

Cited by 30 publications

References 29 publications

2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences

2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences

Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis

Copper-Catalysed Asymmetric 1,4-Addition of Organozinc Compounds to Linear Aliphatic Enones Using 2,2′-Dihydroxy 3,3′-Dithioether Derivatives of 1,1′-Binaphthalene

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