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Article Abstract
The [5,5]-sigmatropic rearrangement is a less-studied reaction and may be strategically utilized to devise unique synthetic processes. Herein, we document a diboron-enabled [5,5]-sigmatropic rearrangement for practical synthesis of BINAM derivatives. Mechanistically, a concerted activation of azonaphthalenes by diboron creates a unique ten-membered transition state, which subsequently triggers a [5,5]-sigmatropic rearrangement. The reaction occurs under mild conditions, and offers operational simplicity, remarkable chemo- and regioselectivities, and good scalability (>10 grams).
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11659970 | PMC |
| http://dx.doi.org/10.1039/d4sc06273f | DOI Listing |
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