synthesis and characterisation of macrocyclic diamino chiral crown ethers合成和描述的大环的二氨基手性冠醚.pdf

Molecules 2004, 9, 513–519 molecules ISSN 1420-3049 Synthesis and Characterisation of Macrocyclic Diamino Chiral Crown Ethers Waldo H. Correa* and Janet L. Scott Centre for Green Chemistry, Monash University, P.O. Box 23, Victoria, 3800, Australia. Tel: (+61) 3 9905 4102, Fax: (+61) 3 9905 4597. * Author to whom correspondence should be addressed: e-mail: waldo.correa@.au Received: 4 March 2004 / Accepted: 10 March 2004 / Published: 31 May 2004 Abstract: A benign and efficient synthesis of chiral macrocyclic ‘aza-crown’ ethers of varying ring size is reported. The synthesis involves a Schiff base condensation of ether linked dialdehydes of varying chain length and (1R,2R)-(–)-1,2-diaminocyclohexane under mild conditions to yield the macrocycles, which are subsequently reduced to yield the diamino analogues. Keywords: Chiral diamino macrocycles, ether linked dialdehydes Introduction In 1998 Kaupp reported the facile solvent-free condensation of aryl amines and benzaldehyde derivatives to produce azo-methines [1]. This is an advantageous and facile route as it negates the generation of excessive waste whilst proceeding more efficiently than corresponding solution phase methodologies. This approach has subsequently been extended to corresponding amine derivatives such as the tetrahydroquinazolines [2]. More recently, we have adopted an analogous, simple procedure that allows for the efficient generation of some macrocycles derived from the reduction of Molecules 2004, 9