We use cookies to ensure that we give you the best experience on our website. By continuing to browse this repository, you give consent for essential cookies to be used. You can read more about our Privacy and Cookie Policy.

Durham e-Theses
You are in:

Some applications and chemistry of (S)-2-(diphenylmethyl)-pyrrolidine

Tavasli, Mustafa (1996) Some applications and chemistry of (S)-2-(diphenylmethyl)-pyrrolidine. Masters thesis, Durham University.



The synthetic utility of (S)-2-(diphenylmethyl)-pyrrolidine (1) and its amide derivative, (S)-2-(diphenylmethyl)-5-oxo-pyrrolidine (2) were examined in two contexts; as chiral auxiliary compounds in asymmetric alkylation reactions and Diels- Alder reactions; as chiral solvating agents (CSAs) for (^1)NMR evaluation of chiral acids and alcohols. In the former case, it was shown that monoalkylation of N-acyl derivatives of (1) and (2) using lithiated bases led to poor diastereoselectivities (1:1 to 1.12:1) and poor yields (28 to 33 %), while alkylation reactions using HMPA proceeded with modest diastereoselectivities (1.49:1 to 4.25:1). The results of the Diels-Alder study remain premature at present. In the latter case, (1) was an excellent chiral solvating agent (CSA) for chiral carboxylic acids, however it was less effective for chiral alcohols. The amide derivative (2) was substantially less effective as a CSA for chiral carboxylic acids and failed completely to resolve chiral alcohols.

Item Type:Thesis (Masters)
Award:Master of Science
Thesis Date:1996
Copyright:Copyright of this thesis is held by the author
Deposited On:24 Oct 2012 15:08

Social bookmarking: del.icio.usConnoteaBibSonomyCiteULikeFacebookTwitter