AI Article Synopsis
- A mixture of AuCl and AgSbF(6) acts as a catalyst for transforming allylic alcohols and alkylamines into pyrrolidine and piperidine derivatives.
- The cyclization of a specific compound led to a high-yield and high-enantiomeric excess product, indicating effective reaction conditions.
- The reaction demonstrates a syn addition mechanism, where the amine bonds in a specific orientation relative to the hydroxyl group, ensuring stereochemical control.
Article Abstract
A 1:1 mixture of (1)AuCl [1 = P(t-Bu)(2)o-biphenyl] and AgSbF(6) catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3429346 | PMC |
| http://dx.doi.org/10.1021/ol103175w | DOI Listing |
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