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ALL–CARBON ENE–TYPE CYCLIZATIONS FROM CYCLOHEXADIENETRICARBONYLIRON DERIVATIVES

Beach, Keith B.
http://orcid.org/0000-0002-1863-3725
http://rave.ohiolink.edu/etdc/view?acc_num=case1463764027

Abstract Details

2016, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Diene-tricarbonyliron chemistry has found great utility in organic synthesis. One area of particular interest utilizes an iron-promoted ene-type reaction to facilitate spirocyclization or tandem double-cyclization when a pendant alkene or diene is available, respectively. Previously in the Pearson lab, spirocyclizations as well as double-cyclizations have been reported starting from compounds containing a heteroatom (O, S, NPh) within the tethered side chain. The work herein focuses on the preparation of cyclization products containing an all-carbon backbone, such as 1. The intriguing aspect of this fundamental research is that synthesis of potential natural product-derivatives may be achieved, in particular those of the angular triquinane class. Investigations of the generality of stereocontrol during Grignard additions used in the formation of 2 will also be described.
Anthony Pearson (Advisor)
Robert Salomon (Committee Chair)
Gregory Tochtrop (Committee Member)
Rajesh Viswanathan (Committee Member)
Yanming Wang (Committee Member)
166 p.
Chemistry
organic chemistry; organic synthesis; diene-tricarbonyliron; cyclohexadiene; Grignard additions; ene-type cyclizations

Recommended Citations

Citations

  • Beach, K. B. (2016). ALL–CARBON ENE–TYPE CYCLIZATIONS FROM CYCLOHEXADIENETRICARBONYLIRON DERIVATIVES [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1463764027

    APA Style (7th edition)

  • Beach, Keith. ALL–CARBON ENE–TYPE CYCLIZATIONS FROM CYCLOHEXADIENETRICARBONYLIRON DERIVATIVES. 2016. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1463764027.

    MLA Style (8th edition)

  • Beach, Keith. "ALL–CARBON ENE–TYPE CYCLIZATIONS FROM CYCLOHEXADIENETRICARBONYLIRON DERIVATIVES." Doctoral dissertation, Case Western Reserve University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=case1463764027

    Chicago Manual of Style (17th edition)

case1463764027
501
© 2016, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.