Synthesen von (1 R )‐ cis ‐3‐(2′,2′‐Dihalovinyl)‐2, 2‐dimethylcyclopropan‐carbonsäuren  via Favorskii ‐Umlagerung von optisch aktiven Cyclobutanonen | Zendy

Greuter Hans | Zendy; Dingwall John | Zendy; Martin Pierre | Zendy; Belluš Daniel | Zendy

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Synthesen von (1 R )‐ cis ‐3‐(2′,2′‐Dihalovinyl)‐2, 2‐dimethylcyclopropan‐carbonsäuren via Favorskii ‐Umlagerung von optisch aktiven Cyclobutanonen

Author(s) -

Greuter Hans,

Dingwall John,

Martin Pierre,

Belluš Daniel

Publication year - 1981

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19810640843

Subject(s) - chemistry , racemization , optically active , amine gas treating , medicinal chemistry , adduct , stereochemistry , organic chemistry

Syntheses of (1 R )‐ cis ‐3‐(2′,2′‐Dihalovinyl)‐2,2‐dimethylcyclopropane Carboxylic Acids via Favorskii ‐rearrangement of Optically Active Cyclobutanones The cis ‐cyclobutanones 7 are resolved by means of optically active amine salts of their sodium hydrogen sulfite adducts. The desired (1 R )‐ cis ‐carboxylic acids 9 are obtained from the (+)‐ cis ‐cyclobutanones 7 via Favorskii ‐rearrangement and HX‐elimination. The recycling of undesired (−)‐ cis ‐cyclobutanones 7 is carried out in good yield by their racemization, thus rendering the total synthesis 1 + 2 → 9 chirally economic.

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