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Stereoselective Synthesis of Diazaheterocycles by Decarboxylative Asymmetric Allylic Alkylation


Sun, Alexander Wang (2019) Stereoselective Synthesis of Diazaheterocycles by Decarboxylative Asymmetric Allylic Alkylation. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/E2YS-GJ06.


The Stoltz group has developed transition-metal catalyzed methods to synthesize quaternary and tetrasubstituted stereocenters over the past fourteen years. Using iridium, palladium, copper, and nickel, the group has synthesized a myriad cyclic and acylic quaternary motifs of incredible synthetic and medicinal utility. This thesis presents several projects that further expand the scope of Pd-catalyzed decarboxylative allylic alkylation and examine its applications to the synthesis of medicinally important small molecules. The synthesis of chiral gem-disubstituted five-, six-, and seven-membered diazaheterocycles is presented. Their utility as building blocks for complex medicinal compounds is highlighted. Then, we explore the utility of gem-disubstituted heterocycles in the context of medicinal chemistry.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Heterocycle, allylic alkylation, allylation, palladium, quaternary center
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Stoltz, Brian M.
Thesis Committee:
  • Dervan, Peter B. (chair)
  • Grubbs, Robert H.
  • Davis, Mark E.
  • Stoltz, Brian M.
Defense Date:19 April 2019
Funding AgencyGrant Number
Record Number:CaltechTHESIS:05132019-140157302
Persistent URL:
Related URLs:
URLURL TypeDescription adapted for Chapter 1.
Sun, Alexander Wang0000-0001-6639-4469
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:11513
Deposited By: Alexander Sun
Deposited On:15 May 2019 18:53
Last Modified:08 Nov 2023 00:39

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