1374313-55-9Relevant academic research and scientific papers
Stereoselective Synthesis of 2 Z,4 e -Configured Dienoates through Tethered Ring Closing Metathesis
Schmidt, Bernd,Aud?rsch, Stephan,Kunz, Oliver
supporting information, p. 4509 - 4518 (2016/12/16)
A two-step sequence leading from racemic allylic alcohols and vinylacetic acid to ethyl (2Z,4E)-dienoates is described. The sequence involves Steglich esterification of the reactants, followed by a one-pot ring closing metathesis-base induced elimination-
One-flask tethered ring closing metathesis-electrocyclic ring opening for the highly stereoselective synthesis of conjugated Z/E-dienes
Schmidt, Bernd,Kunz, Oliver
supporting information; experimental part, p. 1008 - 1018 (2012/03/27)
A one-flask reaction sequence comprising ring closing metathesis (RCM) of butenoates derived from allylic alcohols and a base-mediated ring opening gives 2Z,4E-configured dienoic acids in high yields and stereoselectivities. Application of the method to the synthesis of the natural product fusanolide A suggests that the originally published structure was erroneously assigned and should be revised. Ring closing metathesis (RCM) of butenoates derived from allylic alcohols can be combined with base-induced ring opening in a one-flask sequence. In this way, dienoic acids become accessible in an operationally simple procedure in very high yields and excellent stereoselectivities, with the tether remaining in the product as a valuable functional group for further transformations. Copyright
