347189-30-4Relevant academic research and scientific papers
Divergent reactivity via cobalt catalysis: An epoxide olefination
Jamieson, Megan L.,Hume, Paul A.,Furkert, Daniel P.,Brimble, Margaret A.
supporting information, p. 468 - 471 (2016/02/18)
Cobalt salts exert an unexpected and profound influence on the reactivity of epoxides with dimethylsulfoxonium methylide. In the presence of a cobalt catalyst, conditions for epoxide to an oxetane ring expansion instead deliver homoallylic alcohol products, corresponding to a two-carbon epoxide homologation/ring-opening tandem process. The observed reactivity change appears to be specifically due to cobalt salts and is broadly applicable to a variety of epoxides, retaining the initial stereochemistry. This transformation also provides operationally simple access to enantiopure homoallylic alcohols from chiral epoxides without use of organometallic reagents. Tandem epoxidation-homologation of aldehydes in a single step is also demonstrated.
Simple synthesis of conjugated all-(E)-polyenic aldehydes, ketones, and esters using chemoselective cross-metathesis and an iterative sequence of reactions: Application to the synthesis of navenone B
Bouzbouz, Samir,Roche, Christophe,Cossy, Janine
scheme or table, p. 803 - 807 (2009/06/19)
By using a very simple sequence of reactions such as allylation, acetylation, chemoselective cross-metathesis, and elimination, even and odd conjugated all-(E)-polyenes can be synthesized from very simple alkenes. Georg Thieme Verlag Stuttgart.
Electrophile-induced ether transfer: A new approach to polyketide structural units
Liu, Kai,Taylor, Richard E.,Kartika, Rendy
, p. 5393 - 5395 (2007/10/03)
A strategically novel approach to the formation of syn-1,3-diol mono- and diethers through electrophilic activation of homoallylic alkoxymethyl ethers has been developed. The resulting polyketide-like synthetic fragments are generated in good yield and wi
Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols
Lachance, Hugo,Lu, Xiaosong,Gravel, Michel,Hall, Dennis G.
, p. 10160 - 10161 (2007/10/03)
A general approach for the allylation of aldehydes using stable, air-tolerant camphor-based chiral allylboronates under Sc(OTf)3 catalysis is described. This practical methodology provides both syn and anti propionate units and other homoallylic alcohols with very high levels of diastereo- and enantioselectivity for several substrates, including functionalized aliphatic aldehydes useful toward the elaboration of complex natural products. Copyright
Synthesis of the novel 1,7,9-trioxadispiro[4.1.5.2]-tetradecane ring system present in the spirolides
Caprio, Vittorio,Brimble, Margaret A,Furkert, Daniel P
, p. 4023 - 4034 (2007/10/03)
A synthesis of bis-spiroacetal 13 which constitutes the bis-spiroacetal moiety of the complex marine biotoxins, spirolides 1 and 2 is described. The synthetic strategy adopted is based on assembly of a suitably protected acyclic hydroxyketone precursor. K
