2006年8月
Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl(trimethylsilyl)amide
TETRAHEDRON
- ,
- ,
- 巻
- 62
- 号
- 35
- 開始ページ
- 8351
- 終了ページ
- 8359
- 記述言語
- 英語
- 掲載種別
- 書評論文,書評,文献紹介等
- DOI
- 10.1016/j.tet.2006.06.040
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
Lithium mesitylmethyl(trimethylsilyl)amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoates were also aminated in reasonably high enantioselectivity, while the deprotonation of abstractable proton of enoates caused yield loss of the conjugate amination products, due to the bulkiness and enriched basicity of the lithium amide. Although such steric bulkiness made hard the hydrogenolytic cleavage of a mesitylmethyl-N bond of the adducts, a new protocol comprising N-chlorination-regioselective dehydro-chlorination-transoximation was developed for N-dearylmethylation, giving 3-aminoalkanoates in reasonably good yields. (c) 2006 Elsevier Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/j.tet.2006.06.040
- ISSN : 0040-4020
- Web of Science ID : WOS:000239885200012