811804-97-4Relevant articles and documents
Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols
Shi, Chang-Yun,Yin, Liang,Zhang, Qi,Zhou, Si-Wei
supporting information, p. 26351 - 26356 (2021/11/09)
By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.
Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates
Sun, Jun,He, Fangcheng,Wang, Zhongyao,Pan, Dingwu,Zheng, Pengcheng,Mou, Chengli,Jin, Zhichao,Chi, Yonggui Robin
, p. 6040 - 6043 (2018/06/18)
A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.
Synthesis and antimalarial activity of 6-cycloalkylvinyl substituted 1,2,4-trioxanes
Singh, Chandan,Srivastav, Naveen Chandra,Puri, Sunil K.
, p. 5745 - 5752 (2007/10/03)
6-Cycloalkylvinyl substituted 1,2,4-trioxanes 6-15 have been prepared and tested against multi-drug resistant Plasmodium yoelii in mice. The most active trioxane 11 provides 80% protection to the treated mice. Further derivatization of 11 leads to decreas
A versatile new catalyst for the enantioselective isomerization of allylic alcohols to aldehydes: Scope and mechanistic studies
Tanaka, Ken,Fu, Gregory C.
, p. 8177 - 8186 (2007/10/03)
A new planar-chiral bidentate phosphaferrocene ligand (2) has been synthesized and structurally characterized. The derived rhodium complex, [Rh(cod)(2)]BF4, serves as an effective catalyst for asymmetric isomerizations of allylic alcohols to aldehydes, furnishing improved yields, scope, and enantioselectivities relative to previously reported methods. The catalyst is air-stable and can be recovered at the end of the reaction. Mechanistic studies establish that the isomerization proceeds via an intramolecular 1,3-hydrogen migration and that the catalyst differentiates between the enantiotopic C1 hydrogens.
