200798-57-8Relevant academic research and scientific papers
Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis
Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
experimental part, p. 2197 - 2205 (2011/04/22)
The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g., Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology.
Cycloadditions of highly functionalized C6-synthons to cyclic nitrones
Closa, Montserrat,De March, Pedro,Figueredo, Marta,Font, Josep,Soria, Angeles
, p. 16803 - 16816 (2007/10/03)
The 1,3-dipolar cycloaddition of cyclic nitrones to several C6 α,β- unsaturated esters and lactones with different functionalities has been studied. All these olefins have shown high stereoselectivity, with a predominance of the exo or endo transition state for the cis or trans dipolarophiles, respectively. The antifacial approach is favoured in the reactions with γ-substituted hexenolides and also with the substituted nitrone 21.
