2006 Fiscal Year Final Research Report Summary

STEREOSELECTIVE SYNTHESIS OF NEW CHIRAL COMPOUNDS FROM <-AMINO ACIDS

Research Project

Project/Area Number	16550097
Research Category	Grant-in-Aid for Scientific Research (C)
Allocation Type	Single-year Grants
Section	一般
Research Field	Synthetic chemistry
Research Institution	Tottori University
Principal Investigator	KISE Naoki TOTTORI UNIVERSITY, FACULTY OF ENGINNERING, PROFESSOR, 工学部, 教授 (90177824)
Project Period (FY)	2004 – 2006
Keywords	REDUCTIVE COUPLING / IMINO ESTERS / α-AMINOACIDS / L-ASPARTIC ACID / L-GLUTAMIC ACID / AZETIDINES / β-AMINOALCOHOLS / 1,2-DIAMINES
Research Abstract	1) Electroreductive intramoleculer coupling of aromatic dimethyl imino-a,ω- esters prepared from L-aspartic acid gave chiral azetidines and pyrrolidines, while electroreduction of the corresponding a-amides afforded only chiral pyrrolidines. 2) Electroreductive intramoleculer coupling of aromatic dimethyl imino-a,ω- esters prepared from L-glutamic acid gave chiral azetidines stereo specifically. On the contrary, electroreduction of the corresponding a-amides afforded chiral piperidines. 3) Electroreductive intermolecular coupling of aromatic imines prepared from L-amino acids with acetone gave chiral amionalcohols stereoselectively. 4) Reductive homo-coupling of aromatic iminopeptides prepared from L-amino acids with zinc gave chiral 1,2-diamines stereoselectively.

(2 results)