935749-19-2Relevant articles and documents
Regioselectivity Switch in Palladium-Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross-Coupling
Li, Long,Luo, Pengfei,Deng, Yuhua,Shao, Zhihui
supporting information, p. 4710 - 4713 (2019/03/08)
The first Pd-catalyzed asymmetric allenylic [4+1] cycloaddition was successfully developed. Alternatively, tuning the Pd catalyst switched the reactivity toward an unprecedented [4+3] cycloaddition/cross-coupling. Ligands play a vital role in controlling the reaction pathway, allowing highly selective access to different products from identical substrates. Biological evaluation of the obtained compounds led to the discovery of new antitumor targets. A possible mechanism is proposed, suggesting two interesting catalytic cycles for the cycloaddition with palladium-butadienyls. This study also demonstrated the potential and utility of allenic esters as 1,4-biselectrophiles and C4 synthons for participating in cycloaddition reactions.
Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach
Li, Wenhua,Lin, Zuming,Chen, Long,Tian, Xuechao,Wang, Yan,Huang, Sha-Hua,Hong, Ran
supporting information, p. 603 - 606 (2016/01/20)
A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.
Highly stereoselective facile synthesisl of 2-acetoxy-1,3(E)-alkadienes via a Rh(I)-catalyzed isomerization of 2,3- allenyl carboxylates
Zhang, Xiaobing,Fu, Chunling,Ma, Shengming
supporting information; experimental part, p. 1920 - 1923 (2011/06/21)
A highly stereoselective Rh(I)-catalyzed 1,3-acetoxyl rearrangement of 1,2-allen-3-yl carboxylates leading to 2-acetoxy-1,3(E)-alkadienes has been developed. In addition to the high catalytic efficiency and the scope, the excellent E-selectivity of the do