158249-50-4Relevant articles and documents
Synthesis of N-protected 2-aminohexanesulfonic acid
Constantinou-Kokotou, Violetta
, p. 237 - 240 (1999)
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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.].
A new route for protected amino alcohols from (R)-glycidol. Copper(I) mediated alkylation of 4-tosyloxymethyl-2-oxazolidinone
Iwama,Katsumura
, p. 3363 - 3365 (2007/10/02)
The reaction of (S)-4-tosyloxymethyl-2-oxazolidinone, which was synthesized from (R)-glycidol through (R)-4-benzoyloxymethyl-2-oxazolidinone, with various lithium dialkylcuprate(I)s in THF proceeded smoothly to afford the corresponding protected amino alcohol derivatives in good yield.