Novel and practical asymmetric synthesis of β 2,3 -amino esters using asymmetric Michael addition of chiral amine
| Autor: | Shinzo Hosoi, Toshiki Takano, Narumi Yasuda, Minoru Ozeki, Manabu Node, Honoka Egawa, Tetsuya Kajimoto, Masayuki Yamashita, Hideki Mizutani, Hiroki Iwasaki, Kenji Arimitsu, Naoto Kojima |
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| Rok vydání: | 2017 |
| Předmět: |
Lithium amide
Amino esters 010405 organic chemistry Chemistry education Organic Chemistry Enantioselective synthesis Protonation 010402 general chemistry 01 natural sciences Biochemistry humanities 0104 chemical sciences Adduct chemistry.chemical_compound Drug Discovery Michael reaction Organic chemistry Chiral amine |
| Zdroj: | Tetrahedron. 73:2014-2021 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.02.037 |
| Popis: | A practical method for the synthesis of chiral β2,3-amino esters having various substituents was developed, which is characterized by an asymmetric Michael addition reaction of a chiral lithium amide with trisubstituted (E)-α,β-unsaturated esters. We found that a highly face-selective protonation occurred by the quick addition of water to the enolate intermediate derived from the Michael addition reaction to afford N-protected β2,3-amino esters in moderate to excellent yields. This finding was made possible by the facile preparation of geometrically pure trisubstituted (E)-α,β-unsaturated esters, which was established recently by our group. The subsequent deprotection of the amino group in the Michael adduct by using N-iodosuccinimide (NIS) efficiently provided β2,3-amino esters having various substituents. |
| Databáze: | OpenAIRE |
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