764-38-5Relevant articles and documents
An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A
Kohyama, Aki,Kanoh, Naoki,Kwon, Eunsang,Iwabuchi, Yoshiharu
, p. 517 - 519 (2016)
The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure-activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner's counterpart, and ruthenium-catalyzed ring-closing metathesis.
A Supramolecular Strategy for Selective Catalytic Hydrogenation Independent of Remote Chain Length
Bender, Trandon A.,Bergman, Robert G.,Raymond, Kenneth N.,Toste, F. Dean
supporting information, p. 11806 - 11810 (2019/08/22)
Performing selective transformations on complex substrates remains a challenge in synthetic chemistry. These difficulties often arise due to cross-reactivity, particularly in the presence of similar functional groups at multiple sites. Therefore, there is a premium on the ability to perform selective activation of these functional groups. We report here a supramolecular strategy where encapsulation of a hydrogenation catalyst enables selective olefin hydrogenation, even in the presence of multiple sites of unsaturation. While the reaction requires at least one sterically nondemanding alkene substituent, the rate of hydrogenation is not sensitive to the distance between the alkene and the functional group, including a carboxylate, on the other substituent. This observation indicates that only the double bond has to be encapsulated to effect hydrogenation. Going further, we demonstrate that this supramolecular strategy can overcome the inherent allylic alcohol selectivity of the free catalyst, achieving supramolecular catalyst-directed regioselectivity as opposed to directing-group selectivity.
Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids
Morrill, Louis C.,Smith, Samuel M.,Slawin, Alexandra M. Z.,Smith, Andrew D.
, p. 1640 - 1655 (2014/03/21)
Isothiourea HBTM-2.1 promotes the catalytic asymmetric α- functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.
