90319-52-1Relevant articles and documents
Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion
Zhou, Zijun,Tan, Yuqi,Shen, Xiang,Ivlev, Sergei,Meggers, Eric
, p. 452 - 458 (2020/12/31)
Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. 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 is 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 can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].
Stereoselective Synthesis of Enantiopure Oxazolidinones via Biocatalytic Asymmetric Aminohydroxylation of Alkenes
Zhou, Xiao-Ying,Wan, Nan-Wei,Li, Ying-Na,Ma, Ran,Cui, Bao-Dong,Han, Wen-Yong,Chen, Yong-Zheng
supporting information, p. 4343 - 4348 (2021/08/03)
Chiral oxazolidinones are of significance in both medicinal and synthetic chemistry, while preparing these compounds usually involves using expensive starting materials and harsh reaction conditions. Herein, a one-pot biocatalytic cascade process was developed for stereo- and regioselective aminohydroxylation of diverse alkenes by combining styrene monooxygenase and halohydrin dehalogenase, providing an approach to enantiopure oxazolidinones. (Figure presented.).
Synthesis of Chiral 5-Aryl-2-oxazolidinones via Halohydrin Dehalogenase-Catalyzed Enantio- and Regioselective Ring-Opening of Styrene Oxides
Wan, Nanwei,Zhou, Xiaoying,Ma, Ran,Tian, Jiawei,Wang, Huihui,Cui, Baodong,Han, Wenyong,Chen, Yongzheng
, p. 1201 - 1207 (2020/02/05)
An efficient biocatalytic approach for enantio- and regioselective ring-opening of styrene oxides with cyanate was developed by using the halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1, generating the corresponding chiral 5-aryl-2-oxazoli
