Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation
Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a − f and 5a − d, all containing a proton α to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and α,β-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(β-hydroxyalk...
Saved in:
Published in | Journal of organic chemistry Vol. 63; no. 19; pp. 6704 - 6709 |
---|---|
Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
18.09.1998
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a − f and 5a − d, all containing a proton α to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and α,β-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(β-hydroxyalkyl)benzotriazole derivatives 3a − m, 6a − g, 9a − d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a − m, dienes 7a − j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compoundsthe Wittig, Peterson, and Julia reactionsespecially in the formation of tri- and tetrasubstituted alkenes. |
---|---|
Bibliography: | ark:/67375/TPS-5NZ865V0-Z istex:B51AB6CE6676AC56CD41AAC34E70466FC452D59A |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo980616v |