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ENANTIOSELECTIVE SYNTHESIS AND CYCLOISOMERIZATION OF 1-BICYCLO[1.1.0]BUTAN-1-YL ALKYLAMINES

Yan, Yongzhao (2016) ENANTIOSELECTIVE SYNTHESIS AND CYCLOISOMERIZATION OF 1-BICYCLO[1.1.0]BUTAN-1-YL ALKYLAMINES. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

This dissertation demonstrates the synthesis and application studies of 1-bicyclo[1.1.0]butyl alkylamines. The enantioselective synthesis of 1-bicyclo[1.1.0]butyl alkylamines was achieved by dicarbene addition to enantiomerically enriched propargyl amides. The enantioselective addition of alkynes to imines proceeded well for most N-DPP amides. But the carbene addition suffered from the formation of cyclopropane byproducts. However, a series of silyl-substituted bicyclo[1.1.0]butanes could be synthesized by this methodology in high, reproducible yields. When tethered to an activated alkyne, the silyl-substituted bicyclo[1.1.0]butane undergoes cyclization to form pyrrolidines.
In the application of the 1-bicyclo[1.1.0]butyl alkylamines, a palladium(0)-catalyzed cycloisomerization of bicyclo[1.1.0]butanes and methylenecyclopropanes has been developed. 3-Azaspiro[bicyclo[3.1.0] hexane-6,1'-cyclopropane] is obtained with excellent stereoselectivity. Novel 2,3,3a,6a- tetrahydrocyclopenta[c]pyrrol-4(1H)-one is the product of the cycloisomerization and carbonylation sequence.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Yan, Yongzhaoyoy11@pitt.eduYOY11
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberHorne, Seth Whorne@pitt.eduHORNE
Committee MemberTidgewell, Kevintidgewellk@duq.edu
Date: 3 October 2016
Date Type: Publication
Defense Date: 19 May 2016
Approval Date: 3 October 2016
Submission Date: 7 October 2015
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 203
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: Cycloisomerization, Bicyclo[1.1.0]butane, Palladium, Synthetic Method,
Date Deposited: 03 Oct 2016 21:00
Last Modified: 15 Nov 2016 14:30
URI: http://d-scholarship.pitt.edu/id/eprint/26163

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