Metal‐Free α‐C(sp 3 )−H Functionalized Oxidative Cyclization of Tertiary  N , N ‐Diarylamino Alcohols: Construction of  N,N ‐Diarylaminotetrahydropyran Scaffolds | Zendy

Afzal Sualiha | Zendy; Venkanna Arramshetti | Zendy; Park Hyeunggeun | Zendy; Kim Mihyun | Zendy

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Metal‐Free α‐C(sp 3 )−H Functionalized Oxidative Cyclization of Tertiary N , N ‐Diarylamino Alcohols: Construction of N,N ‐Diarylaminotetrahydropyran Scaffolds

Author(s) -

Afzal Sualiha,

Venkanna Arramshetti,

Park Hyeunggeun,

Kim Mihyun

Publication year - 2016

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.201500392

Subject(s) - chemistry , hypervalent molecule , anomer , iodine , stereochemistry , oxidative phosphorylation , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry

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 α‐C(sp 3 )−O bond formation, with the loss of only two H atoms. This efficient synthetic method broadens the scope of viable α‐C(sp 3 )−H functionalized amines to include conformational‐bias‐free substrates.

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