1011301-86-2Relevant articles and documents
Vinylogous Reactivity of Cyclic 2-Enones: Organocatalysed Asymmetric Addition to 2-Enals to Synthesize Fused Carbocycles
Sofiadis, Manolis,Kalaitzakis, Dimitris,Sarris, John,Montagnon, Tamsyn,Vassilikogiannakis, Georgios
, p. 6742 - 6746 (2019)
A method for asymmetric and site selective annulations at the γ and γ′ positions of cyclic 2-enones with α,β-unsaturated aldehydes has been developed. The organocatalysed [3+3]-annulations proceed with high levels of regio-, diastereo-, and enantioselectivity, affording a series of high value fused carbocycles. Further elaboration gave key lactones (both bridged and fused).
Chemodivergent Synthesis of One-Carbon-Extended Alcohols via Copper-Catalyzed Hydroxymethylation of Alkynes with Formic Acid
Jin, Xin,Fu, Hong-Chen,Wang, Mei-Yan,Huang, Shouying,Wang, Yue,He, Liang-Nian,Ma, Xinbin
supporting information, p. 4997 - 5001 (2021/06/28)
The development of selective catalytic reactions that utilize easily available reagents for the efficient synthesis of alcohols is a long-standing goal of chemical research. Here an intriguing strategy for the chemodivergent copper-catalyzed hydroxymethylation of alkynes with formic acid and hydrosilane has been developed. By simply tuning the amount of formic acid and reaction temperature, distinct one-carbon-extended primary alcohols, that is, allylic alcohols and β-branched alkyl alcohols, were produced with high levels of Z/E-, regio-, and enantioselectivity.
Boron-Templated Dimerization of Allylic Alcohols to Form Protected 1,3-Diols via Acid Catalysis
Nazari, S. Hadi,Forson, Kelton G.,Martinez, Erin E.,Hansen, Nicholas J.,Gassaway, Kyle J.,Lyons, Nathan M.,Kenney, Karissa C.,Valdivia-Berroeta, Gabriel A.,Smith, Stacey J.,Michaelis, David J.
supporting information, p. 9589 - 9593 (2019/12/02)
We report an unprecedented boron-templated dimerization of allylic alcohols that generates a 1,3-diol product with two stereogenic centers in high yield and diastereoselectivity. This acid-catalyzed reaction is achieved via in situ formation of a boronic ester intermediate that facilitates selective cyclization and formation of a cyclic boronic ester product. High yields are observed with a variety of allylic alcohols, and mechanistic studies confirm the role of boron as a template for the reaction.
