On the use of deuterium isotope effects in chemical synthesis Journal Article
| Authors: | Dudley, G. B.; Danishefsky, S. J.; Sukenick, G. |
| Article Title: | On the use of deuterium isotope effects in chemical synthesis |
| Abstract: | The decreased kinetic acidity of deuterium relative to hydrogen can be used to gain an advantage in the reductive cyclization of an alkenyllithium species onto a ketone. The intermediate alkenyllithium can add to the carbonyl or abstract an α-proton, giving rise to two products. The yield of the cyclized product can be increased, and the formation of the uncyclized by-product can be suppressed, by replacing the acidic protons with deuterons prior to cyclization. © 2002 Elsevier Science Ltd. All rights reserved. |
| Keywords: | cyclization; isotope; synthesis; proton; acidity; hydrogen; deuterium; carbonyl derivative; article |
| Journal Title: | Tetrahedron Letters |
| Volume: | 43 |
| Issue: | 32 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2002-08-05 |
| Start Page: | 5605 |
| End Page: | 5606 |
| Language: | English |
| DOI: | 10.1016/s0040-4039(02)01114-0 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 14 November 2014 -- Source: Scopus |
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