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Stereoisomeric flavour compounds XLV: Structure analysis of 2‐alkoxy‐5‐alkyl‐tetrahydrofurans
Author(s) -
Palm Ursula,
Mosandl Armin,
Bensch Wolfgang
Publication year - 1991
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530030113
Subject(s) - chemistry , alkoxy group , absolute configuration , acetal , alkyl , enantiomer , stereochemistry , diastereomer , organic chemistry
Abstract The synthesis of several 2‐alkoxy‐5‐alkyl‐tetrahydrofurans is of interest in our investigations of structure–function relationships of chiral flavour compounds. For the preparation of the enantiomeric acetals the unambiguous configurational assignment of the cis and trans series of these compounds is indispensable. By means of crystalline acetal derivatives the absolute structure of a model compound in the cis and the trans configuration is revealed by X‐ray measurement and correlated with the corresponding cis and trans configurated aroma compounds. The first complete structure elucidation of the class of 2‐alkoxy‐5‐alkyltetrahydrofurans has been carried out.