Synthesis of chiral molecular clefts. New armatures for biomimetic systems

CS Wilcox, LM Greer, V Lynch

Index: Wilcox, Craig S.; Greer, Laurie M.; Lynch, Vincent Journal of the American Chemical Society, 1987 , vol. 109, # 6 p. 1865 - 1867

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Citation Number: 58

Abstract

Figure 1.'H NMR data, 360 MHz, for 4a and 4c in CDC1,. Differences between the ester inside isomer and the ester outside isomer are readily apparent. by SnC1,/C2H50H. 8 The resulting racemic amine 3 was treated with formaldehyde and HCl to provide, in 42% yield, three diastereomeric Troger's base analogues 4a, 4b, and 4, easily separable by chromatography, and consistently obtained in a 1: 2: 1 ratio (Scheme I).