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Die absolute Konfiguration von 1‐ 2 H 1 ‐Äthanol
Author(s) -
Weber H.,
Seibl J.,
Arigoni D.
Publication year - 1966
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.19660490115
Subject(s) - chemistry , stereospecificity , hydroboration , alcohol dehydrogenase , ethanol , chirality (physics) , stereochemistry , yeast , deuterium , alcohol , organic chemistry , catalysis , biochemistry , physics , quantum mechanics , nambu–jona lasinio model , chiral symmetry breaking , quark
( S )‐l‐ 2 H 1 ‐Ethanol (6) has been prepared in three steps from (–)‐ erythro ‐(2 R ,3 S )‐3‐ 2 H 1 ‐butan‐2‐ol (2) , itself available from cis ‐butene by asymmetric hydroboration. In enzymatic tests with yeast alcohol dehydrogenase this deuterated ethanol proved to be indistinguishable from the laevorotatory isomer. This establishes the ( S )‐chirality of the latter and at the same time defines the stereospecificity of the yeast alcohol dehydrogenase.