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Zinc-catalyzed allenylations of aldehydes and ketones.
- Source :
-
Organic letters [Org Lett] 2011 Oct 21; Vol. 13 (20), pp. 5616-9. Date of Electronic Publication: 2011 Sep 26. - Publication Year :
- 2011
-
Abstract
- The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective B/Zn exchange to generate a propargyl zinc intermediate, the addition to the electrophile effectively competes with propargyl-allenyl zinc equilibration. The utility of the methodology was demonstrated by application to a rhodium-catalyzed [4+2] cycloaddition.<br /> (© 2011 American Chemical Society)
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 13
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 21942658
- Full Text :
- https://doi.org/10.1021/ol202343c