《Atroposelective Total Synthesis of the Fourfold ortho-Substituted Naphthyltetrahydroisoquinoline Biaryl O,N-Dimethylhamatine》 was published in Chemistry – A European Journal in 2019. These research results belong to Slack, Eric D.; Seupel, Raina; Aue, Donald H.; Bringmann, Gerhard; Lipshutz, Bruce H.. Quality Control of (R)-Oxiran-2-ylmethanol The article mentions the following:
A stereoselective total synthesis of O,N-dimethylhamatine (I), an analog of an axially chiral naphthylisoquinoline natural biaryl product from tropical Ancistrocladus lianas, is reported. The route features a late-stage atropo-diastereoselective biaryl bond formation. Generation of this especially challenging, sterically hindered tetra-ortho-substituted array was achieved by using Nolan’s (IPr*NHC)PdCinCl pre-catalyst under mild Negishi coupling conditions. Discussion is offered regarding the selectivity obtained exptl. and predicted from DFT calculations on the key biaryl coupling step that leads to the desired M-diastereomer. In the experiment, the researchers used many compounds, for example, (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Quality Control of (R)-Oxiran-2-ylmethanol)
(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Quality Control of (R)-Oxiran-2-ylmethanol
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