Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 25, Pages 8404-8407Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b03986
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Funding
- National Science Foundation [CHE-1362709, CHE-01162222]
- Margaret Strauss Kramer Fellowship from NYU Department of Chemistry
- Global Research Initiatives, NYU
- NYU Florence
- National Institutes of Health [OD016343]
- Materials Research Science and Engineering Center (MRSEC) program of the National Science Foundation (NSF) [DMR-0820341, DMR-1420073]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1362709] Funding Source: National Science Foundation
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Seven-membered-ring trans-alkenes undergo rapid, uncatalyzed carboboration reactions to form trialkylboranes as single diastereomers. In contrast with other trialkylboranes, which can ignite in the presence of oxygen, these trialkylboranes are stable in air. Hindered trialkylboranes can undergo reverse hydroboration reactions to form allylic silanes or can be oxidized to afford highly substituted triols. This reaction sequence permits the construction of compounds with up to five consecutive stereocenters. Control experiments and computational studies support a concerted mechanism for the migratory insertion of the alkene into the carbon-boron bond, similar to the mechanism for hydroboration.
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