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

doi:10.1021/acscatal.1c04483

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

23 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 language	English
Pages (from-to)	536-543
Number of pages	8
Journal	ACS Catalysis
Volume	12
Issue number	1
DOIs	https://doi.org/10.1021/acscatal.1c04483
Publication status	Published - 2022 Jan 7

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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

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.",

author = "Tanpure, {Sudhakar Dattatray} and Kuo, {Tung Chun} and Cheng, {Mu Jeng} and Liu, {Rai Shung}",

note = "Funding Information: We thank the Ministry of Education (MOE 110QR001I5) and the Ministry of Science and Technology (MOST 109-2634-F-007-023), Taiwan, for financial support of this work. Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

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AU - Kuo, Tung Chun

AU - Cheng, Mu Jeng

AU - Liu, Rai Shung

N1 - Funding Information: We thank the Ministry of Education (MOE 110QR001I5) and the Ministry of Science and Technology (MOST 109-2634-F-007-023), Taiwan, for financial support of this work. Publisher Copyright: © 2021 American Chemical Society

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

Abstract

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