Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents
Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents
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.
density functional calculations, flow chemistry, natural products, rearrangement, ytterbium
13076-13079
Packard, Emma
996d6dd2-803e-4892-8f88-f97b123a8ed4
Pascoe, David D.
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Maddaluno, Jacques
37e0bd01-a822-42e2-832d-69dc876fcefa
Harrowven, David C.
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2 December 2013
Packard, Emma
996d6dd2-803e-4892-8f88-f97b123a8ed4
Pascoe, David D.
15deb860-264b-4bdd-8b73-10fddabdadeb
Maddaluno, Jacques
37e0bd01-a822-42e2-832d-69dc876fcefa
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Packard, Emma, Pascoe, David D., Maddaluno, Jacques and Harrowven, David C.
(2013)
Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents.
Angewandte Chemie, 52 (49), .
(doi:10.1002/anie.201307193).
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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e-pub ahead of print date: 23 October 2013
Published date: 2 December 2013
Keywords:
density functional calculations, flow chemistry, natural products, rearrangement, ytterbium
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 358879
URI: http://eprints.soton.ac.uk/id/eprint/358879
ISSN: 0044-8249
PURE UUID: d0fbf052-3049-4681-9cb9-00b5683bb458
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Date deposited: 14 Oct 2013 12:58
Last modified: 15 Mar 2024 02:47
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Author:
Emma Packard
Author:
David D. Pascoe
Author:
Jacques Maddaluno
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