Zhou, Zijun; Tan, Yuqi; Shen, Xiang; Ivlev, Sergei; Meggers, Eric published the article 《Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion》. Keywords: organoruthenium complex preparation; ethoxycarbonylamino benzoate ruthenium catalyst enantioselective heterocyclization; oxazolidinone preparation.They researched the compound: 2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol( cas:35836-73-8 ).Safety of 2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:35836-73-8) here.
Herein, a general intramol. C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcs was reported. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method was applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates was subsequently be hydrolyzed to obtain chiral β-amino alcs. The method was very practical as the catalyst was easily synthesized on a gram scale and was recycled after the reaction for further use. The synthetic value of the new method was demonstrated with the asym. synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcs. that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.
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Reference:
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