Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 10, Pages 4854-4860Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300725v
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- National Science Foundation [CHE-0847686]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0847686] Funding Source: National Science Foundation
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Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess-Martin periodinane (DMP) in CHCl3 followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.
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