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Diastereoselective and Enantioselective Aldol Condensations with Bis-Cyclopentadienyl Zirconium Enolates


McGee, Lawrence Ray (1982) Diastereoselective and Enantioselective Aldol Condensations with Bis-Cyclopentadienyl Zirconium Enolates. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/e2qn-kh88.


Bis-cyclopentadienyl zirconium enolates undergo aldol condensation to afford erythro aldol adducts regardless of enolate configuration. Enolates of chiral amides afford high levels of asymmetric induction at the erythro stereo-centers. Mild hydrolysis of the chiral auxiliaries occurs via intramolecular assistance by hydroxyl neighboring groups in the chiral auxiliary. The absolute configurations of the erythro-aldol products have been determined by independent correlations to compounds of known absolute configuration. A cyclic metal-centered transition state model has been developed which accounts for the stereoselectivity observed with zirconium enolates.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Evans, David A.
Thesis Committee:
  • Evans, David A. (chair)
  • Gagne, Robert R.
  • Dougherty, Dennis A.
  • Collins, Terrence J.
  • Roberts, John D.
Defense Date:17 June 1981
Record Number:CaltechTHESIS:10212019-154636979
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:11836
Deposited By: Mel Ray
Deposited On:21 Oct 2019 23:51
Last Modified:01 Dec 2021 21:52

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