Stereoselective construction of sterically hindered oxaspirocycles: Via chiral bidentate directing group-mediated C(sp3)-O bond formation

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Title
Stereoselective construction of sterically hindered oxaspirocycles: Via chiral bidentate directing group-mediated C(sp3)-O bond formation
Author(s)
Yechan Kim; Seoung-Tae Kim; Dahye Kang; Te-ik Sohn; Eunyoung Jang; Mu-Hyun Baik; Sungwoo Hong
Publication Date
2018-02
Journal
CHEMICAL SCIENCE, v.9, no.6, pp.1473 - 1480
Publisher
ROYAL SOC CHEMISTRY
Abstract
The systematic investigation of chiral bidentate auxiliaries has resulted in the discovery of a chiral 2,2-dimethyl-1-(pyridin-2-yl)propan-1-amine-derived directing group that enables stereoselective palladium(ii)-catalyzed intramolecular C(sp3)-O bond formation. This new chiral directing group exhibited high reactivity in the activation of methylene C(sp3)-H bonds with excellent levels of stereoselectivity (a diastereomeric ratio of up to 39:::1), which allowed the construction of a wide range of oxaspirocycles. Mechanistic investigations were also conducted to elucidate the reaction mechanism and understand the origin of the diastereoselectivity. DFT calculations suggest that only modest levels of diastereoselectivity are accomplished at the rate-determining C-H metalation-deprotonation step and the d.r. is further enriched at the reductive elimination step. © 2018 The Royal Society of Chemistry
URI
https://pr.ibs.re.kr/handle/8788114/4737
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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