AI Article Synopsis
- - Two methods are described for synthesizing ()-(+)-1,2-epoxy-5-hexene using cheap and accessible materials.
- - The first method involves a two-step process with mCPBA epoxidation and chiral resolution, yielding 24-30%.
- - The second method starts with ()-epichlorohydrin, achieving 55-60% yield and high purity through ring-opening and closure reactions. Both methods have been tested successfully on scales of 100-200 grams.
Article Abstract
Herein, we describe two practical approaches to synthesize ()-(+)-1,2-epoxy-5-hexene from inexpensive and readily available raw materials and reagents. The first approach is a two-step sequence, involving an epoxidation with -chloroperoxybenzoic acid (mCPBA) and a chiral resolution with (salen)Co(II), producing ()-(+)-1,2-epoxy-5-hexene in 24-30% overall yield. The second approach utilizes readily available ()-epichlorohydrin as the starting material and features an epoxide ring-opening reaction with allylMgCl and the NaOH-mediated ring closure reaction. Development of this two-step process affords -(+)-1,2-epoxy-5-hexene in overall isolated yields of 55-60% with an exceptional purity profile. Both approaches have been successfully demonstrated on 100-200 g scales.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11334172 | PMC |
| http://dx.doi.org/10.1021/acs.oprd.4c00101 | DOI Listing |
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