Studies on A Novel Asymmetric Cycloaddition Using Optically Active <alpha> , <beta> -Unsaturated Sulfoxides
| Project/Area Number |
59570888
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Toyama Medical & Pharmaceutical University |
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Principal Investigator |
KOIZUMI Toru Professor, 薬学部, 教授 (40012611)
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| Co-Investigator(Kenkyū-buntansha) |
TAKAYAMA Hiromitsu Assistant, 薬学部, 助手 (90171561)
ARAI Yoshitsugu Assistant, 薬学部, 助手 (10115157)
TAKEUCHI Yoshio Associate Professor, 薬学部, 助教授 (20111750)
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| Project Period (FY) |
1984 – 1986
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| Project Status |
Completed (Fiscal Year 1986)
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| Budget Amount *help |
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1986: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1985: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1984: ¥1,100,000 (Direct Cost: ¥1,100,000)
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| Keywords | <alpha> , <beta> -Unsaturated Sulfoxides / Asymmetric Diels-Alder Reaction / Asymmetric Cycloaddition / 高ジアステレオ選択性 |
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| Research Abstract |
Asymmetric Diels-Alder reaction using substituted arylsulfinylethenes (vinyl sulfoxides) has been studied. The high diastereoselectivity was interpreted in terms of the favored direction of the diene approach from the side of the sulfur lone pair in energetically favored s-cis or s-trans conformers and the conformational preferences in vinyl sulfoxides are rationalized on the basis of dipole-dipole and/or steric interactions between S-O and the substituents at <alpha> or <beta> position.
On the otherhand, the use of 2-pyridylsulfinyl group in place of p-tolyl-sulfinyl group enhanced the reactivity considerably and the high diastereoselectivity was also maintained by the cycloaddition with furan to give 7-oxabicyclo [2.2.1]hept-5-ene-2-carboxylic acid derivatives. The application of the asymmetric Diels-Alder reaction to the chiral synthesis of some biologically active natural products was achieved.
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Report
(1 results)
Research Products
(11 results)
