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Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents.

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.

SUBMITTER: Packard E

PROVIDER: S-EPMC4285119 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents.

Packard Emma E Pascoe David D DD Maddaluno Jacques J Gonçalves Théo P TP Harrowven David C DC

Angewandte Chemie (International ed. in English) 20131023 49

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. ...[more]

PMID: 24155206

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