Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents

Emma Packard; David D. Pascoe; Jacques Maddaluno; Théo P. Gonçalves; David C. Harrowven

doi:10.1002/anie.201307193

Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents

Emma Packard, David D. Pascoe, Jacques Maddaluno, Théo P. Gonçalves, David C. Harrowven^*

^*Corresponding author for this work

Chemistry

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

14 Scopus citations

Abstract

Changing course: While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R=tBu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (-)-mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.

Original language	English (US)
Pages (from-to)	13076-13079
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	49
DOIs	https://doi.org/10.1002/anie.201307193
State	Published - Dec 2 2013

Keywords

density functional calculations
flow chemistry
natural products
rearrangement
ytterbium

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201307193

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abstract = "Changing course: While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R=tBu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (-)-mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.",

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AU - Packard, Emma

AU - Pascoe, David D.

AU - Maddaluno, Jacques

AU - Gonçalves, Théo P.

AU - Harrowven, David C.

PY - 2013/12/2

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KW - density functional calculations

KW - flow chemistry

KW - natural products

KW - rearrangement

KW - ytterbium

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Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents

Abstract

Keywords

ASJC Scopus subject areas

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