7547-96-8Relevant articles and documents
Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution
Amalian, Jean-Arthur,Bressy, Cyril,Charles, Laurence,Desrues, Titouan,Liu, Xueyang,Monnier, Valérie,Pons, Jean-Marc,Quintard, Adrien
supporting information, p. 4332 - 4336 (2021/06/27)
The stereocontrol of tertiary alcohols represents a recurrent challenge in organic synthesis. In the present paper, we describe a simple, efficient, and indirect method to enantioselectively prepare tertiary alcohols through a chiral isothiourea catalyzed
A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates
Chen, Jian,Liang, Yong,Ma, Jiawei,Meng, Lingpu,Zhang, Yao,Zhu, Shaolin
supporting information, p. 3171 - 3188 (2021/11/16)
Ligand-controlled reactivity plays an important role in transition-metal catalysis, enabling a vast number of efficient transformations to be discovered and developed. However, a single ligand is generally used to promote all steps of the catalytic cycle (e.g., oxidative addition, reductive elimination), a requirement that makes ligand design challenging and limits its generality, especially in relay asymmetric transformations. We hypothesized that multiple ligands with a metal center might be used to sequentially promote multiple catalytic steps, thereby combining complementary catalytic reactivities through a simple combination of simple ligands. With this relay catalysis strategy (L/L?), we report here the first highly regio- and enantioselective remote hydroarylation process. By synergistic combination of a known chain-walking ligand and a simple asymmetric cross-coupling ligand with the nickel catalyst, enantioenriched α-aryl alkylboronates could be rapidly obtained as versatile synthetic intermediates through this formal asymmetric remote C(sp3)-H arylation process.
Synthesis of enantiopure cyclic amino acid derivatives via a sequential diastereoselective Petasis reaction/ring closing olefin metathesis process
Morozova, Veronika A.,Beletskaya, Irina P.,Titanyuk, Igor D.
, p. 349 - 354 (2017/02/18)
A novel approach to the synthesis of enantiopure cyclic amino esters is reported. The utilization of allylboronic acid together with (S)-α-methylbenzylamine as a chiral auxiliary in the Petasis/Mannich reaction led to the formation of allylglycine derivatives in good yield and with high diastereoselectivity. Subsequent esterification, N-allylation followed by ring-closing metathesis (RCM) reaction enabled the preparation of enantiomerically pure cyclic α-amino acid derivatives.