Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 44, Pages 7367-7371Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901435
Keywords
Internal allylic alcohols; Silanes; Copper catalysis; Stereospecific hydroboration; Diastereoselectivity
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Funding
- National Natural Science Foundation of China [21702105]
- Natural Science Foundation of Jiangsu Province, China [BK20170981]
- Nanjing Tech University
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An effective Cu-catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2-trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3-diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).
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