In 2017,Diehl, Julian; Brueckner, Reinhard published 《Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence》.European Journal of Organic Chemistry published the findings.Product Details of 78191-00-1 The information in the text is summarized as follows:
An established route to enantiomerically pure β-hydroxy ketones proceeds through the asym. hydrogenation of β-keto esters, an ester/amide exchange, and the use of the resulting β-hydroxy amide for the acylation of an organometallic compound The authors shortened this route by showing that β-keto Weinreb amides are hydrogenated with up to 99% ee in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(μ-Cl)3}- (0.5 mol-%) at room temperature/5 bar. These Weinreb amides were prepared by seemingly obvious yet unprecedented condensations of lithiated N-methoxy-N-methylacetamide with carboxylic chlorides (51-87% yield). The resulting β-hydroxy Weinreb amides were used for the acylation of organolithium and Grignard reagents. They thus gave enantiomerically pure β-hydroxy ketones (28 examples). A selection of these compounds gave anti-1,3-diols after another C:O bond hydrogenation, or syn-1,3-diols by a Narasaka-Prasad reduction In the experiment, the researchers used N-Methoxy-N-methylacetamide(cas: 78191-00-1Product Details of 78191-00-1)
N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Product Details of 78191-00-1
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics