1992
DOI: 10.1248/cpb.40.562
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Payne rearrangement route to the optically active oxirane precursor for the preparation of trizole antifungals.

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Cited by 13 publications
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“…As an alternative to isolation, the mesylation reaction mixture could be immediately treated with sodium hydroxide to form the epoxide 12 in good yield and purity. This synthetic sequence was demonstrated to be superior to previous routes to 12 , which required chromatographic purification. ,,,, …”
Section: Resultsmentioning
confidence: 93%
“…As an alternative to isolation, the mesylation reaction mixture could be immediately treated with sodium hydroxide to form the epoxide 12 in good yield and purity. This synthetic sequence was demonstrated to be superior to previous routes to 12 , which required chromatographic purification. ,,,, …”
Section: Resultsmentioning
confidence: 93%
“…From the synthetic perspective, nucleophilic ring-opening of the (2 R ,3 S )-epoxide 2 allows rapid access to diverse triazole analogues, thus rendering this chiral epoxide an exceptionally valuable and versatile intermediate in industrial synthesis and medicinal chemistry (Figure ). , Apart from the traditional resolution method and chiral pool strategy, catalytic asymmetric synthesis of 2 has garnered considerable attention from the synthetic community for its high efficiency and atom economy, albeit with formidable challenges. In 1995, Bennett and co-workers reported the pioneering catalytic asymmetric synthesis of (2 R ,3 S )-epoxide 2a through Sharpless–Katsuki epoxidation of ( Z )-alkene 5 (Figure A) . However, the laborious and low-yielding isomerization from ( E )-alkene 4 to ( Z )-alkene 5 , coupled with the moderate enantioselectivity of the epoxidation (76% ee), adversely affected the synthetic efficiency.…”
Section: Introductionmentioning
confidence: 99%