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Metal-Free -C(sp(3))-H Functionalized Oxidative Cyclization of Tertiary N,N-Diarylamino Alcohols: Construction of N,N-Diarylaminotetrahydropyran Scaffolds
- Issue Date
- Feb-2016
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- 6-exo-trig; metal-free reactions; oxidative cyclization; tertiary amines; -C(sp(3))-H functionalization
- Citation
- ASIAN JOURNAL OF ORGANIC CHEMISTRY, v.5, no.2, pp.232 - 239
- Journal Title
- ASIAN JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 5
- Number
- 2
- Start Page
- 232
- End Page
- 239
- ISSN
- 2193-5807
- Abstract
- Herein, we report an efficient synthetic method for the preparation of anomeric N,N-diarylaminotetrahydropyran scaffolds. The free radical 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/hypervalent iodine(III)- or TEMPO/I-2-mediated oxidative cyclization of tertiary amino alcohols was used to construct N,N-diarylaminotetrahydropyrans through -C(sp(3))-O bond formation, with the loss of only two Hatoms. This efficient synthetic method broadens the scope of viable -C(sp(3))-H functionalized amines to include conformational-bias-free substrates.
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Related Researcher
- Kim, Mi Hyun
- Pharmacy (Dept.of Pharmacy)