Organocatalytic asymmetric reactions using (S)-homoproline
| Project/Area Number |
17550028
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Ibaraki University |
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Principal Investigator |
ORIYAMA Takeshi IBARAKI University, College of Science, Professor, 理学部, 教授 (90185687)
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| Project Period (FY) |
2005 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2006: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2005: ¥2,400,000 (Direct Cost: ¥2,400,000)
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| Keywords | Organocatalyst / Proline / Michael addition / Homoproline / Thiol / Solvent-free / Asymmetric reaction / プロリン系有機溶媒 / 不斉1,4-付加反応 / ヒドロキシプロリン / 疎水性 / 水中 / (S)-ホモプロリン / 不斉マイケル付加反応 |
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| Research Abstract |
Recently, proline or its derivatives-catalyzed asymmetric carbon-carbon bond-forming reactions such as aldol reaction, the Michael addition, and Mannich-type reaction were studied intensively by many organic chemists. Excellent enantioselectivity was attained in various types of organocatalytic asymmetric reactions, but the Michael addition has some serious limitations. For example, there are scattered examples over 90% ee, and substrate generality is not so high. On the other hand, we have developed a novel asymmetric Michael addition reaction of ketone to b-nitrostyrene and its derivatives using (5)-homoproline as a chiral organocatalyst. The reaction was performed in a highly diastereoselective and enantioselective manner over 90% ee. Furthermore, we have developed solvent-free organocatalytic asymmetric conjugate addition of thiols to a, b-unsaturated aldehydes. In the presence of well-designed organocatalyst, the reaction proceeds without any organic solvents, giving the corresponding chiral sulfides in almost enantiomerically pure form (up to 99% ee). Moreover, b, b-disubstituted a, b-unsaturated aldehydes also reacted with phenylmethanethiol. This method is environment-friendly, economical, and convenient.
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Report
(3 results)
Research Products
(11 results)
