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Facile preparation of optically pure diamines and their applications in asymmetric aldol reactions

✍ Scribed by Quan-Zhong Liu; Xue-Lian Wang; Shi-Wei Luo; Bao-Lei Zheng; Da-Bin Qin


Book ID
104095956
Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
165 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis


A family of optically pure diamines with tertiary-primary amine motif has been synthesized from optically pure binaphthol and amino acids. The catalysts are highly tunable in structure and has demonstrated high efficiency in direct aldol reactions. Thus, a variety of aldehydes or methyl 2-oxoacetates reacted with acetone in the presence of 10 mol % of catalyst and 20 mol % TFA, furnishing the desired alcohols in up to 99% yield with excellent enantioselectivities (up to 96% ee).


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## Abstract An efficient homocoupling of imines to give vicinal diamines promoted by low‐valent niobium, generated by treatment of NbCl~5~ with zinc powder, is described. The desired products were obtained in good to excellent yields. Dihydroisoquinoline derivatives also gave the coupling products