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Adelaide Research and Scholarship
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Schools and Disciplines
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School of Chemistry and Physics
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Chemistry
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Chemistry Publications
Permanent link to this item:
http://hdl.handle.net/2440/4549
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| Type: | Article |
| Title: | 1,2-dioxines as masked cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones |
| Author: | Greatrex, Ben W.
Kimber, Marc Colin
Taylor, Dennis K.
Fallon, Gary D.
Tiekink, Edward Richard Tom |
| Citation: | Journal of Organic Chemistry, 2002; 67:5307-5314 |
| Publisher: | American Chemical Society |
| Issue Date: | 2002 |
| ISSN: | 0022-3263 |
| School/Discipline: | School of Chemistry and Physics : Chemistry
School of Agriculture, Food and Wine : Wine and Horticulture |
| Abstract: | Addition of highly stabilized ester nucleophiles to 1,2-dioxines affords good to high yields of γ-lactones with high diastereoselectivity. Heterolytic or homolytic cleavage of the 1,2-dioxines under appropriate conditions generates the key reactive cis γ-hydroxy enones, which ultimately afford the observed γ-lactones. Diastereoselectivity is installed as a result of anti 1,4-addition by the ester enolate to the cis enones followed by intramolecular cyclization. The reaction is tolerant of a range of substitution patterns on the 1,2-dioxine while a broad range of esters are also accommodated. In addition to the synthesis of racemic γ-lactones, highly enantioenriched γ-lactones can also be synthesized when chiral cobalt(II) catalysts are employed for the initial homolytic ring-opening of the 1,2-dioxine. |
| Description: | Copyright © 2002 American Chemical Society |
| RMID: | 0020020004 |
| DOI: | 10.1021/jo0200421 |
| Published version: | http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/2002/67/i15/abs/jo0200421.html |
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| Appears in Collections: | Chemistry Publications
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