Construction of Asymmetric Space

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"Construction of Asymmetric Space" plays a central role in asymmetric synthesis. Investigations have been made on the construction of efficient asymmetric spaces and its applications to design novel methods of asymmetric synthesis and catalytic asymmetric synthesis. Following results were obtained.1) Multidentate chiral lithium amides and chiral amines that can form efficient chiral spaces by chelation were designed and synthesized. Novel asymmetric reactions, such as asymmetric deprotonation, alkylation, and protonation, were developed using these chiral bases. These asymmetric reactions were further developed to catalytic asymmetric reacation. 2) Evidences for the existence of chiral enolates from optically active alpha-amino acid derivatives by deprotonation were found. The new concept "Chiral Memory" was developed and applied to the synthsis of optically active compounds. 3) To utilize sugar derivatives as useful compounds having efficient chiral spaces, highly stereoselective glycosidation methods giving the product in high yields were developed. 4) Chiral di-ethers and amodophosphine derivatives providing efficient chiral spaces were designed and synthesized. They were proved to be useful for the catalytic asymmetric conjugate addition reactions of organolithium and organocopper reagents. 5) Experimental ant theoretical studies were made on the nature of asymmetric spaces for the purpose to deisgn novel asymmetric synthesis. Highly stereoselective addition reactions were developed using novel organocopper reagents and allylzinc complexes.