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Enantio- and regioselective propargylic and allylic functionalization

Zhu, Jin (2024) Enantio- and regioselective propargylic and allylic functionalization. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

The rapid development of enantioselective allylic or propargylic C − H functionalization methods offers great opportunities for introducing functional groups to readily available starting materials in a stereodefined manner. In this dissertation, we synthesized N-heterocyclic molecules from simple alkynes with good regioselectivity utilizing stoichiometric Fe intermediates. The achievement of highly enantioselective allylic functionalization of non-activated alkenes was realized through the synergistic combination of Fe and Ir catalysts. In addition, we systematically investigated the enantioselective propargylic functionalization with Ir catalysis, thereby expanding the scope pf propargylic functionalization. A wide range of alkynes underwent successful propargylic allylation and silylation, enabling the formation of 1,5-dienes, propargylsilanes and allenylsilanes with good enantioselective and stereoselective control.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhu, Jinjiz172@pitt.edujiz1720000-0003-2792-6332
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWang, Yimingyimingw@pitt.edu
Committee MemberBrummond, Kay M.kbrummon@pitt.edu
Committee MemberFloreancig, Paul E.florean@pitt.edu
Committee MemberHuryn, Donna M.huryn@pitt.edu
Date: 10 January 2024
Date Type: Publication
Defense Date: 4 December 2023
Approval Date: 10 January 2024
Submission Date: 10 November 2023
Access Restriction: 2 year -- Restrict access to University of Pittsburgh for a period of 2 years.
Number of Pages: 440
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: C-H functionalization, propargylic functionalization, enantioselectivity, diastereoselectivity
Date Deposited: 10 Jan 2024 14:16
Last Modified: 10 Jan 2024 14:16
URI: http://d-scholarship.pitt.edu/id/eprint/45668

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