165457-66-9Relevant articles and documents
Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters
Farley, Alistair J. M.,Sandford, Christopher,Dixon, Darren J.
supporting information, p. 15992 - 15995 (2016/01/15)
The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated α-substituted acrylate esters catalyzed by a bifunctional iminophosphorane organocatalyst under mild conditions is described. The strong Br?nsted basicity of the iminophosphorane moiety of the catalyst provides the necessary activation of the alkyl thiol pro-nucleophile, while the two tert-leucine residues flanking a central thiourea hydrogen-bond donor facilitate high enantiofacial selectivity in the protonation of the transient enolate intermediate. The reaction is broad in scope with respect to the alkyl thiol, the ester moiety, and the α-substituent of the α,β-unsaturated ester, affords sulfa-Michael adducts in excellent yields (up to >99%) and enantioselectivities (up to 96% ee), and is amenable to decagram scale-up using catalyst loadings as low as 0.05 mol %.
Total synthesis of jerangolid D
Pospisil, Jiri,Marko, Istvan E.
, p. 3516 - 3517 (2008/01/01)
A short and convergent synthesis of jerangolid D is described. As key steps, a Blaise reaction is employed to construct the lactone ring, a diastereoselective multicomponent Sakurai condensation leads to the dihydropyran ring, and the skipped diene is ass
Total synthesis of brevetoxin A: Part 1: First generation strategy and construction of BCD ring system
Nicolaou,Bunnage, Mark E.,McGarry, Daniel G.,Shi, Shuhao,Somers, Patricia K.,Wallace, Paul A.,Chu, Xin-Jie,Agrios, Konstantinos A.,Gunzner, Janet L.,Yang, Zhen
, p. 599 - 617 (2007/10/03)
Discussed herein is our first generation strategy for the total synthesis of brevetoxin A. This approach relies upon dissection of the molecule at the nine-membered ring site (ring E). A Wittig coupling of requisite polycyclic fragments 3 and 4 followed b
