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STUDIES ON AZA-CYCLOADDITION:PART 1. INTRAMOLECULAR KETENE-IMINE CYCLOADDITIONPART 2. IMINIUM ION-MEDIATED [4+2] CYCLOADDITION

Park, Jung-hyun (2011) STUDIES ON AZA-CYCLOADDITION:PART 1. INTRAMOLECULAR KETENE-IMINE CYCLOADDITIONPART 2. IMINIUM ION-MEDIATED [4+2] CYCLOADDITION. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

Part 1. Intramolecular Ketene-Imine CycloadditionThe ketene-imine cycloaddition reactions, developed previously by the Nelson group, have beenextended to the intramolecular cycloaddition of the ketene-imine cycloaddition. Initial resultsshowed that the intramolecular cycloaddition exhibited excellent enantioselectivity, but it wassuffered from poor diastereoselectivity. Later, it was shown that proper functionality on thetether of the substrate could improve diastereoselectivity.Part 2. Iminium Ion-Mediated [4+2] CycloadditionThe N-alkenyl iminium ion cycloaddition reaction (AIC reaction), developed previously by theNelson group, was further investigated for the more detailed understaniding. As a result, tworeaction pathways (Diels-Alder pathway and oxo-Diels-Alder pathway) of the AIC reaction werefound when carbamate-protected N-alkenyl iminium ion was employed as a 4Ĉ-electroncomponent. Based on this observation, efficient methods to turn off either one of the tworeaction pathways were proposed.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Park, Jung-hyunjup19@pitt.eduJUP19
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scott Gsgnelson@pitt.eduSGNELSON
Committee MemberDoemling, Alexanderasd30@pitt.eduASD30
Committee MemberWilcox, Craig Sdaylite@pitt.eduDAYLITE
Committee MemberCohen, Theodorecohen@pitt.eduCOHEN
Date: 31 January 2011
Date Type: Completion
Defense Date: 27 August 2011
Approval Date: 31 January 2011
Submission Date: 18 November 2010
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
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: Diels-Alder; imine; ketene
Other ID: http://etd.library.pitt.edu/ETD/available/etd-11182010-170358/, etd-11182010-170358
Date Deposited: 10 Nov 2011 20:05
Last Modified: 15 Nov 2016 13:51
URI: http://d-scholarship.pitt.edu/id/eprint/9715

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