Practical, Catalytic Enantioselective Hydrogenation to Synthesize N-Unprotected β-Amino Esters
Practical and simple catalytic enantioselective hydrogenation reactions to synthesize N-unprotected β-amino esters have been developed: (1) asymmetric hydrogenation of N-unprotected β-enamine ester and (2) asymmetric direct reductive amination of β-keto esters using ammonium salts. A Ru–DM-SEGPHOS c...
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| Veröffentlicht in: | Organic process research & development 2011-09, Vol.15 (5), p.1130-1137 |
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| container_title | Organic process research & development |
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| creator | Matsumura, Kazuhiko Zhang, Xiaoyong Hori, Kiyoto Murayama, Toshiyuki Ohmiya, Tadamasa Shimizu, Hideo Saito, Takao Sayo, Noboru |
| description | Practical and simple catalytic enantioselective hydrogenation reactions to synthesize N-unprotected β-amino esters have been developed: (1) asymmetric hydrogenation of N-unprotected β-enamine ester and (2) asymmetric direct reductive amination of β-keto esters using ammonium salts. A Ru–DM-SEGPHOS complex was used as the catalyst in both cases and gave high enantioselectivity, high reactivity, and wide substrate applicability. These protocols greatly reduced reaction time and waste compared to conventional synthetic routes. The direct reductive amination route was demonstrated on a >100 kg scale. |
| doi_str_mv | 10.1021/op2001035 |
| format | Article |
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A Ru–DM-SEGPHOS complex was used as the catalyst in both cases and gave high enantioselectivity, high reactivity, and wide substrate applicability. These protocols greatly reduced reaction time and waste compared to conventional synthetic routes. 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Process Res. Dev</addtitle><date>2011-09-16</date><risdate>2011</risdate><volume>15</volume><issue>5</issue><spage>1130</spage><epage>1137</epage><pages>1130-1137</pages><issn>1083-6160</issn><eissn>1520-586X</eissn><abstract>Practical and simple catalytic enantioselective hydrogenation reactions to synthesize N-unprotected β-amino esters have been developed: (1) asymmetric hydrogenation of N-unprotected β-enamine ester and (2) asymmetric direct reductive amination of β-keto esters using ammonium salts. A Ru–DM-SEGPHOS complex was used as the catalyst in both cases and gave high enantioselectivity, high reactivity, and wide substrate applicability. These protocols greatly reduced reaction time and waste compared to conventional synthetic routes. The direct reductive amination route was demonstrated on a >100 kg scale.</abstract><pub>American Chemical Society</pub><doi>10.1021/op2001035</doi><tpages>8</tpages></addata></record> |
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| title | Practical, Catalytic Enantioselective Hydrogenation to Synthesize N-Unprotected β-Amino Esters |
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