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Die durch Lewis-Säuren katalysierte Cyclisierung von Geranylaceton (1975)

Schulte-Elte, Karl H. ; Ohloff, Günther

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 58 (1975), S. 18-27

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Geranylacetone (1a, 1b) in the presence of a Lewis acid, undergoes a novel cyclization reaction to yield the two diastereomers 9-oxabicyclo[3·3·1]nonene 2 and 3 as main products. The formation of 2 and 3 is not stereospecific, i.e. both isomers 1a and 1b produce the same product mixture (2/3 ∼ 2:1 ratio).This is in contrast to the known Brønsted-acid catalyzed cyclization of 1, leading exclusively to the chromenes 4 and 5 in a stereospecific reaction.The reaction mechanisms and the structural assignments are discussed.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19750580104

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