Synthesis of Optically Pure Enantiomers Using Chiral Ureas
| Project/Area Number |
03640438
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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 |
有機化学一般
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| Research Institution | CHIBA University |
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Principal Investigator |
YAMADA Kazutoshi Chiba University, Department of Materials Science, Professor, 工学部, 教授 (60009230)
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| Co-Investigator(Kenkyū-buntansha) |
KOHMOTO Shigeo Chiba University, Department of Materials Science, Associate Professor, 工学部, 助教授 (90195686)
YAMAMOTO Makoto Chiba University, Department of Materials Science, Professor, 工学部, 教授 (50039294)
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| Project Period (FY) |
1991 – 1992
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| Project Status |
Completed (Fiscal Year 1992)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1991: ¥1,800,000 (Direct Cost: ¥1,800,000)
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| Keywords | Asymmetric Aldol reaction / Asymmetric Diels-Alder reaction / Michael addition / Imidazolidinone / exo-methylenehydantoin / Chiral derivatizing agent / Type II photocyclization / カルボジイミド / 不斉アルド-ル反応 / 不斉ディ-ルス・アルダ-反応 / 1.4ー付加反応 |
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| Research Abstract |
Using Chiral urea derivatives, the following diastereoselective synthesis and a convenient separation of diastereomers by a conventional column chromatography were accomplished.
(1) Diastereoselective aldol addition reaction using chiral acylureas; This method was applied to the two step synthesis of (+) Blastmaycinolactol.
(2) Chiral carbodiimide as an effective chiral derivatizing agent; N,N'-bis[(s)-l-phenylethyl]- carbodiimide was found to be a very useful chiral derivatizing agent, which made an easy separation of diastereomers of alpha-amino acids and alpha-halo acids by a conventional column chromatography.
(3) Highly enantioselective Aldol reaction using imidazolidinone as a new chiral Auxiliary; Aldol addition reaction of almost perfect stereo control (>99% diastereoselectivity) was developed.
(4) Chiral hydantoin as a new dienophile for Diels-Alder Reaction; A new synthetic method of chiral exo-methylenehydantoin from chiral carbodiimides and alpha-ketoacids was established and the exo-methylenehydantoin thus obtained was applied for Diels-Alder reaction to prepare chiral bicyclic alpha-amino acid derivatives.
(5) Conjugated addition reaction of alkylaluminum compounds to exo-methylenehydantoin; Mono and Double conjugated additions of aluminum reagents to exo-methylenehydantoin were found out and this two modes of addition was effectively controlled.
(6) Three component coupling reaction carbodiimide, monomethyl maleate, and alcohol; This coupling afforded N-(aminocarbony)aspartates.
(7) Asymmetric type II photocyclization of acrylylureas; It was found that the stereochemistry of the carbon atom where a hydrogen atom to be abstracted in type II photocyclization was retained to give a chiral beta-lactam.
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Report
(3 results)
Research Products
(17 results)
