✦ LIBER ✦
Mechanistic implications of stereospecific 1,5-hydrogen-atom transfer in the formation of an unusual allene/enoate photoproduct
✍ Scribed by Curtis A. Hastings; Josef D. Ringgenberg; Erick M. Carreira
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 219 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Irradiation of allene-enoate 1 affords alkyne 3 as the major photoproduct.
Selectively deuterated analog d-I affords a single diastereomer on inadiation. This result .~bim~/ical a sl~pwise mechanism for enantioselective [2+2]-photocycloadditioas involving a 1,4intermediate 2 which collapses to products more rapidly than it unde~oes reversion to stinting material, resulting in the observed high levels of asymmetric induction.