| Project/Area Number |
13640533
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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 | Kyoto Institute of Technology |
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Principal Investigator |
AMIKO Atsushi KYOTO INSTITUTE OF TECHNOLOGY, GRADUATE SCHOOL OF ENGINEERING, ASSOCIATE PROFESSOR, 工芸科学研究科, 助教授 (30184203)
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| Project Period (FY) |
2001 – 2003
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| Project Status |
Completed (Fiscal Year 2003)
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| Budget Amount *help |
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2003: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2001: ¥1,200,000 (Direct Cost: ¥1,200,000)
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| Keywords | double aldol reaction / boron-mediated albol reaction / carboxylic ester / asymmetric synthesis / chiral triol of C3-symmetry / chiral synthon / doubly borylated enolate / carbon-bound enolate / chiral recognition / 分子不斉 / 金属錯体 / 炭素結合エノレート |
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| Research Abstract |
We have devised new asymmetric boron-mediated double aldol reactions complementarily useful for the synthesis of aliphatic and aromatic substituted chiral triols of C3-symmetry, which are potential precursors for the study of asymmetric catalysis and chiral recognition, via double aldol reactions of a chiral acetate ester or a chiral acetyloxazolidinone.
Chiral dendrimenrs having a chiral triol of C3-symmetry as a core element with 3, 5-disubstituted benzyl ether type dendrone of the 3^<rd> to 5^<th> generation were synthesized. The chiroptical properties of these dendrimers were examined and shown to exibhit the "dilution effect", eveidence of their of "molecular chirality being not observed.
Tris-pyridine, and tris-bipyridine substituted compounds were synthesized to examine properties of their metal complexes. Tris-2-pyridylmethyl and tris-3-pyridylmethl substituted chiral triols were synthesized. Their copper complexes were shown to be 1: 1, and 2: 1 complex, respectively, by ESI-MS measurement. Catalytic of these complexes was examined.
Tris-6'-methyl-6-(2, 2 -bipyridylmethyl) substituted triols did not afford Ru complex upon treatment with 5'-methyl-5-chloromethy-2, 2'bipyridine proceeded only low yield (<10%). An alternate route using Stille coupling of stannylpyridine and 2-bromopyridylmethyl substituted chiral triols will be executed.
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