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Aspects of the Reduction of Double Bonds Using Cob (I)alamin as Catalys
Author(s) -
Fischli Albert
Publication year - 1982
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.19820650839
Subject(s) - chemistry , double bond , aqueous solution , acetic acid , catalysis , derivative (finance) , ring (chemistry) , medicinal chemistry , solvent , stereochemistry , organic chemistry , economics , financial economics
The olefinic system in 3β‐methoxy‐4‐cholesten‐6 a ‐ol ( 2 ) is reduced using cob (I)alamin ( 1 ( I ); see Scheme 1 ) as catalyst, aqueous acetic acid as solvent and metallic zinc as electron source ( cf. Schemes 2 and 3 ). Experimental evidence for an attack of 1 ( I ) on both faces of the double bond is presented. By the same catalyst (1 R )‐10, 10‐dimethyl‐2‐pinene‐ 10‐carbonitrile ( 9 ) is first transformed to the menthene derivative 11 (see Schemes 4 and 5 ). The ring opening is then followed by a fast saturation of the disubstituted olefinic system in 11 , and ultimately the remaining double bond is reduced in a slow reaction. The cis‐configurated saturated menthane derivative 16 is the main final product ( 16 / 17 ≈ 10:1).