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Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents

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
0044-8249
13076-13079
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
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), 13076-13079. (doi:10.1002/anie.201307193).

Record type: Article

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
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 14 Oct 2013 12:58
Last modified: 15 Mar 2024 02:47

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Contributors

Author: Emma Packard
Author: David D. Pascoe
Author: Jacques Maddaluno

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