| Project/Area Number |
11554025
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
Organic chemistry
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| Research Institution | Osaka Prefecture University, Faculty of Integrated Arts & Sciences |
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Principal Investigator |
UEMURA Motokazu Osaka Prefecture University, Department of Chemistry, Professor, 総合科学部, 教授 (90047241)
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| Co-Investigator(Kenkyū-buntansha) |
KONOIKE Toshiro Shionogi & CO., LTD, General Manager, 研究所所長
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| Project Period (FY) |
1999 – 2001
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| Project Status |
Completed (Fiscal Year 2001)
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| Budget Amount *help |
¥14,000,000 (Direct Cost: ¥14,000,000)
Fiscal Year 2001: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 2000: ¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1999: ¥8,700,000 (Direct Cost: ¥8,700,000)
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| Keywords | vancomycin / atropisomer / planar chiraliy / cross-coupling / 軸不斉ビアリール / アレーンクロム錯体 / コルペンスアミン / アルカロイド / コンペンスアミン |
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| Research Abstract |
Axially chiral biaryls are significantly important not only as chiral ligands or auxiliaries in asymmetric reactions but also for biologically active natural products. For the asymmetric synthesis of axially chiral biaryls, we have investigated the cross-coupling of the planar chiral arylhalide chromium tricarbonyl complexes with arylboronic acids. Thus, palladium (0)-mediated Suzuki-Miyaura cross-coupling of planar chiral (2, 6-disubstituted bromobenzene) chromium complexes with o-substituted arylboronic acids gave stereoselectively axially chiral mono Cr(CO)3-complexed biaryls. The axial stereochemistry of the cross-coupling products was found to be largely dependent on the steric bulkiness of ortho substituent of arylboronic acids and reaction conditions. The overall process gives a promising approach for the preparation of both atropisomers stereoselectively starting from a single planar chiral (arene)chromium complex. By utilizing these methodologies, biologically active axially chiral natural products, steganone, korupensamine and axially chiral A-B ring system of vancomycin were stereoselectively synthesized.
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