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Cob(I)alamin Differentiating Alkenes During Saturation
Author(s) -
Schönholzer Peter,
Süss Daniel,
Wan Terence S.,
Fischli Albert
Publication year - 1984
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.19840670306
Subject(s) - chemistry , oxime , catalysis , saturation (graph theory) , rationalization (economics) , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , combinatorics , philosophy , mathematics , epistemology
The olefins 2, 7, 11 , and 19 , have been reduced using catalytic amounts of cob(I)alamin( I(I) ). During a slow saturation, the catalyst is able to differentiate the two diastereotopic faces of the endocyclic double bonds in 11 ( t 1/2 4 h,. cf. Scheme 3 ) are reduced much faster. A rationalization of the data can be obtained formulating tertiary alkylcobalamins as intermediates. Of the oxime 6 ( cf. Scheme 2 ) and the p ‐ bromobenzoate 23 ( cf. Scheme 5 ) the structures have been determined by X‐ray analysis.