21866-72-8Relevant academic research and scientific papers
Stereodefined rhodium-catalysed 1,4-H/D delivery for modular syntheses and deuterium integration
Cheng, Bao,Fang, Huayi,Ma, Shengming,Qian, Hui,Wang, Weiyi,Yu, Yibo,Zhang, Xue
, p. 586 - 594 (2021/07/17)
Deuterium-incorporated compounds are of high interest owing to their importance in the pharmaceutical industry, organic synthesis and materials science. So far, the integration of deuterium into the inert, saturated magic methyl or methylene groups of covalent molecules remains challenging. Here, we present a 1,4-H delivery of allylic metallic species to provide a highly stereoselective and straightforward approach to 3-methyl-2(E)-enals or -enones from readily available 2,3-allenols and organoboronic acids. The reaction accommodates many synthetically versatile functional groups as well as multi-pharmacophores, and is not limited to the formation of 3-methyl derivatives. By applying 1,4-H or D delivery, deuterium atom(s) from differently deuterated allenols can be edited into the methyl or methylene groups of versatile organic skeletons, resulting in the efficient formation of 4-monodeuterated, 1,4- and 4,4-doubly deuterated, and 4,4,4-triply deuterated 2(E)-enals or -enones. These powerful platform molecules can provide straightforward paths to other deuterated compounds for different purposes. [Figure not available: see fulltext.].
Rh-Catalyzed Asymmetric Hydrogenation of β-Branched Enol Esters for the Synthesis of β-Chiral Primary Alcohols
Liu, Chong,Yuan, Jing,Zhang, Jian,Wang, Zhihui,Zhang, Zhenfeng,Zhang, Wanbin
supporting information, p. 108 - 111 (2018/01/17)
An asymmetric hydrogenation of β-branched enol esters has been developed for the first time, providing a new route for the synthesis of β-chiral primary alcohols. Using a (S)-SKP-Rh complex bearing a large bite angle and enol ester substrates possessing an O-fomyl directing group, the desired products were obtained in quantitative yields and with excellent enantioselectivities.
Gold catalyzed Heck-coupling of arenediazonium o-benzenedisulfonimides
Barbero, Margherita,Dughera, Stefano
, p. 295 - 301 (2018/01/12)
Diazonium salts, and precisely arenediazonium o-benzenedisulfonimides, have been used for the first time as efficient electrophilic partners in gold catalyzed Heck-coupling reactions. The synthetic protocol was general, easy and gave the target products in satisfactory yields. Mechanistic insights revealed the fundamental roles of the o-benzenedisulfonimide anion as an electron transfer agent thath promotes a radical pathway that does not require the presence of photocatalysts or external oxidants.
Asymmetric Catalytic Aza-Diels–Alder/Ring-Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis
Li, Yang,Barl?se, Casper,J?rgensen, Julie,Carlsen, Bj?rn Drei?,J?rgensen, Karl Anker
supporting information, p. 38 - 41 (2017/01/09)
An asymmetric catalytic aza-Diels–Alder/ring-closing cascade reaction between acylhydrazones and in situ formed trienamines is presented. The reaction proceeds through a formal aza-Diels–Alder cycloaddition, followed by a ring-closing reaction forming the hemiaminal ring leading to chiral bicyclic azaheterocycles in moderate to good yield (up to 71 %), good enantio- (up to 92 % ee) and diastereoselectivity (up to >20:1 d.r.). Furthermore, transformations are presented to show the potential application of the formed product.
