期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 51, 页码 21254-21259出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c09923
关键词
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资金
- Knut and Alice Wallenberg Foundation [2018.0066]
- Swedish Research Council [2017-04235]
- Wenner-Gren Foundation [UPD2019-0149]
- Swedish Research Council [2017-04235] Funding Source: Swedish Research Council
- Vinnova [2017-04235] Funding Source: Vinnova
Chiral alpha-substituted allylboronic acids were synthesized by asymmetric homologation of alkenylboronic acids using CF3/TMS-diazomethanes in the presence of BINOL catalyst and ethanol. The chiral alpha-substituted allylboronic acids were reacted with aldehydes or oxidized to alcohols in situ with a high degree of chirality transfer. The oxygen-sensitive allylboronic acids can be purified via their isolated diaminonaphthalene (DanH)-protected derivatives. The highly reactive purified allylboronic acids reacted in a self-catalyzed reaction at room temperature with ketones, imines, and indoles to give congested trifluoromethylated homoallylic alcohols/amines with up to three contiguous stereocenters.
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