26682-82-6Relevant academic research and scientific papers
A new type of stereoselectivity in Baeyer-Villiger reactions: Access to E- and Z-olefins
Zhang, Zhi-Gang,Roiban, Gheorghe-Doru,Acevedo, Juan Pablo,Polyak, Iakov,Reetz, Manfred T.
supporting information, p. 99 - 106 (2013/03/14)
A new concept for accessing configurationally defined trisubstituted olefins has been developed. Starting from a common ketone precursor of the type 4-ethylidenecyclohexanone, Baeyer-Villiger monooxygenases are employed as catalysts in diastereoselective Baeyer-Villiger reactions leading to the corresponding E- or Z-configurated lactones. Wild-type cyclohexanone monooxygenase (CHMO) as catalyst delivers the E-isomers and a directed evolution mutant the opposite Z-isomers. Subsequent transition metal-catalyzed chemical transformations of a key product containing a vinyl bromide moiety provide a variety of different trisubstituted E- or Z-olefins. A model based on QM/MM sheds light on the origin of this unusual type of diastereoselectivity. In contrast to this biocatalytic approach, traditional Baeyer-Villiger reagents such as m-CPBA fail to show any selectivity, 1:1 mixtures of E- and Z-olefins being formed. Copyright
Spiro compounds or salts thereof and preventives/remedies for autoimmune diseases and AP-1 inhibitors containing the same
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, (2008/06/13)
The spiro compounds of the present invention represented by the general formula: wherein A, R2, R3, R4, R5, R6and n are as defined in the specification, exhibit an AP-1 activity inhibitory action and, based on the AP-1 inhibitory action, suppresses the expression of a wide variety of genes and are useful as an agent for treating and preventing autoimmune diseases with lessoned side reactions.
A convenient synthesis of some 1,4-disubstituted 7-oxabicyclo[2.2.1]heptanes
Baker,Harris
, p. 2015 - 2023 (2007/10/02)
An efficient synthesis of a 1,4-disubstituted 7-oxabicyclo[2.2.1]heptane intermediate and its subsequent conversion to a potential PAF antagonist is described.
