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March 29, 2026Synthesis

Control of Periselectivity and Stereoselectivity of Intramolecular 8+2 Cycloadditions

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Authors

PBPauline BianchiJKJosh KimKHK. N. Houk

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Overview

Computational investigation reveals periselectivity in cycloadditions, highlighting ester's dual role.

Key Points

  • This research aims to understand how periselectivity and stereoselectivity in intramolecular cycloadditions are controlled.
  • Utilized density functional theory (DFT) for computational analysis
  • Conducted frontier molecular orbital (FMO) analysis
  • Investigated various cycloaddition pathways
  • Confirmed exclusive [8+2] cycloaddition pathway is favored
  • Identified alternative pathways like [6+4], [4+2], and [2+4] as thermodynamically disfavored
  • Established that ester substituent facilitates specific stereoselective interactions

Cite This Study

Bianchi et al. (2026) studied this question.

synapsesocial.com/papers/69c8c25dde0f0f753b39ca0chttps://doi.org/10.1055/a-2826-1682
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