RESEARCH ARTICLE

 

Application of (S,S)-pentacycloundecane bis(4-phenyloxazoline) as a novel chiral ligand for catalysis of the asymmetric Diels-Alder reaction of cyclopentadiene with 3-acryloyl-2-oxazolidinone

 

 

Per I. Arvidsson^I; Thavendran Govender^II; Hendrik G. Kruger^III; Glenn E.M. Maguire^III; Tricia Naicker^III

^IDepartment of Biochemistry and Organic Chemistry, Uppsala University, Uppsala S-751 23, Sweden
^IISchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, Republic of South Africa
^IIISchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, Republic of South Africa

 

 

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ABSTRACT

The synthesis of the novel C₁ symmetric (S,S)-pentacycloundecane bis(4-phenyloxazoline) ligand 5 and its evaluation as a chiral Lewis acid catalyst in the benchmark asymmetric Diels-Alder reaction between 3-acryloyloxazolidin-2-one (6)and cyclopentadiene (7) is reported. From the various metal salts screened the anhydrous magnesium perchlorate complex emerged as the best catalyst. The endo-cycloadduct product 8 was afforded in 81% enantiomeric excess with an endo:exo ratio of 98:2. An extensive screening of various metal ions as complexing agents was performed and is also reported.

Key words: Pentacycloundecane, oxazolines, chiral catalysis, Diels-Alder reaction

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Acknowledgements

This work was supported by Grants from the National Research Foundation Gun 2073251 (South Africa), the South African/Swedish Research Links Programme (Gun 2072799) and the University of KwaZulu-Natal.

 

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Received 7 October 2008
Revised 25 November 2008A
Accepted 18 December 2008

 

 

* To whom correspondence should be addressed. E-mail: kruger@ukzn.ac.za