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Synthetic Process Development of (R)-(+)-1,2-Epoxy-5-hexene: An Important Chiral Building Block.

ABSTRACT: Herein, we describe two practical approaches to synthesize (R)-(+)-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 meta-chloroperoxybenzoic acid (mCPBA) and a chiral resolution with (salen)Co(II), producing (R)-(+)-1,2-epoxy-5-hexene in 24-30% overall yield. The second approach utilizes readily available (R)-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 R-(+)-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.

SUBMITTER: Guthrie D

PROVIDER: S-EPMC11334172 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Synthetic Process Development of (R)-(+)-1,2-Epoxy-5-hexene: An Important Chiral Building Block.

Guthrie Daryl D Saathoff John M JM Sahani Rajkumar Lalji RL Nunes De Souza Aline A Cook Daniel W DW Hochstetler Samuel R SR Burns Justina M JM Moazeni-Pourasil Roudabeh Sadat RS Wierzbicki Janie J Ahmad Saeed S Laidlaw G Michael GM Gupton B Frank BF Shanahan Charles S CS Klumpp Douglas A DA Jin Limei L

Organic process research & development 20240801 8

Herein, we describe two practical approaches to synthesize (R)-(+)-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 meta-chloroperoxybenzoic acid (mCPBA) and a chiral resolution with (salen)Co(II), producing (R)-(+)-1,2-epoxy-5-hexene in 24-30% overall yield. The second approach utilizes readily available (R)-epichlorohydrin as the starting material and featur ...[more]

PMID: 39171130

Dataset Information

Synthetic Process Development of (R)-(+)-1,2-Epoxy-5-hexene: An Important Chiral Building Block.

Publications

Synthetic Process Development of (<i>R</i>)-(+)-1,2-Epoxy-5-hexene: An Important Chiral Building Block.

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