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- Title
Chiral N, N′-Dioxide-Scandium(III) Complex-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of ortho-Hydroxybenzyl Alcohols with C3-Substituted N-Protected Indoles.
- Authors
Zheng, Jianfeng; Lin, Lili; Dai, Li; Yuan, Xiao; Liu, Xiaohua; Feng, Xiaoming
- Abstract
The first Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted indoles is described. A chiral N, N′-dioxide Sc(OTf)3 complex served not only to promote formation of ortho-quinone methides ( o-QMs) in situ but also induced the asymmetry of the reaction. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99 % yield and 99 % ee. A range of functional groups were also tolerated under the mild reaction conditions. Moreover, this strategy gives concise access to enantioenriched indole-fused benzoxocines.
- Subjects
CHEMICAL alcohol synthesis; SCANDIUM compounds; INDOLE compounds; FRIEDEL-Crafts reaction; ASYMMETRIC synthesis; SUBSTITUENTS (Chemistry); SCANDIUM catalysts; LEWIS acids
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 50, p18254
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201604088