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Flavin Catalysis Employing an N(5)‐Adduct: an Application in the Aerobic Organocatalytic Mitsunobu Reaction
Author(s) -
März Michal,
Babor Martin,
Cibulka Radek
Publication year - 2019
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.201900397
Subject(s) - chemistry , flavin group , adduct , mitsunobu reaction , catalysis , combinatorial chemistry , organocatalysis , organic chemistry , enantioselective synthesis , enzyme
An artificial flavin system has been firstly proved to employ an N(5)‐adduct for a catalytic transformation. This mode of catalysis occurs in some flavoenzymes but it is unknown in chemocatalysis, still exclusively using only C(4a)‐adducts. In our report, an ethylene‐bridged biomimetic flavin has been shown to participate in the Mitsunobu esterification reaction as an alternative to dialkyl azodicarboxylate. The reaction occurs via a flavin N(5)‐triphenylphosphane adduct and is catalytic from the point of view of the flavin, which is regenerated by oxygen. This approach distinguishes from other catalytic Mitsunobu reaction procedures which require an extra catalytic system.