Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Constructions of Bicyclo[3.2.1]oct-6-ene Frameworks via (4 + 3)-Cycloadditions

Sudhakar Dattatray Tanpure, Tung Chun Kuo, Mu Jeng Cheng, Rai Shung Liu

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A one-pot construction of bicyclo[3.2.1]oct-6-ene frameworks involves gold-catalyzed (4 + 3)-cycloadditions between 2-(1-alkynyl)-2-alken-1-ones and substituted cyclopentadienes; diastereoselectivity (dr >25:1) and enantioselectivity (up to 99.9% ee) are achieved with a chiral gold catalyst. Our DFT calculations suggest a three-step ionic mechanism for the cycloadditions of gold-containing 1,3-dipoles with cyclopentadienes, in which an exo-spatial arrangement is preferable.

Original languageEnglish
Pages (from-to)536-543
Number of pages8
JournalACS Catalysis
Volume12
Issue number1
DOIs
Publication statusPublished - 2022 Jan 7

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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