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Stereochemical Analysis of the Enzymic Reduction of the Double Bond of α‐ and β‐Substituted Nitrostyrenes and α‐Ethoxycinnamaldehyde through Deuterium Labelling Experiments
Author(s) -
Brenna Elisabetta,
Fronza Giovanni,
Fuganti Claudio,
Gatti Francesco G.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000442
Subject(s) - chemistry , double bond , deuterium , alkoxy group , hydride , stereochemistry , hydroxymethyl , molecule , medicinal chemistry , hydrogen bond , catalysis , hydrogen , organic chemistry , alkyl , quantum mechanics , physics
2 H NMR studies and comparison with authentic labelled reference compounds prepared from the ( Z )‐acetamido‐cinnamic acid 10 and from ( Z )‐2‐ethoxy‐3‐(4‐methoxyphenyl)prop‐2‐en‐1‐ol ( 14 ), respectively, by catalytic syn reduction with deuterium gas show that the baker's yeast‐mediated saturation in the presence of deuterated water of the double bond of ( E )‐α‐(hydroxymethyl)nitrostyrene ( 2 ) and of the ( Z )‐α‐ethoxycinnamaldehyde ( 3 ) leads to (2 R ,3 R )‐[2,3‐ 2 H 2 ]‐3‐(4‐methoxyphenyl)‐2‐nitropropan‐1‐ol ( 5 ) and to(1 R ,2 S ,3 R )‐[1,2,3‐ 3 H 2 ]‐2‐ethoxy‐3‐(4‐methoxyphenyl)propan‐1‐ol ( 6 ), respectively, thus supporting an anti mode of hydrogen addition across the activated double bond, with hydride delivery in β‐position respect to the activating group from the upper side of the molecule.