Bicyclo[2.2.1] heptane-carboxamides : Pathway to chiral ketones and cyclopentanes

ISBN-13: 9783838328003 / Angielski / Miękka / 2009 / 76 str.

Martin Thuo Mwangi

Opis

This book summarizes efforts toward the chiral synthesis of norcamphor and analogues. Intermediate amide was resolved and X-ray structure of the enantiomers solved. The absolute configuration of the ketones was inferred from that of corresponding amide precursor. The conversion of the precursors to the ketones was performed and proved to be stereospecific. This was based on the hydrolysis of chloronitriles to ketones via amides. Since chlorine gives anomalous dispersion of X-rays, the chlorinated intermediates could be used to assign absolute configuration of the ketones. The generated synthesized chiral ketones play a critical role in the synthesis of disubstituted cyclopentanes as demonstrated in the synthesis of stereoselective hydroxylation of the bicyclic amides and subsequent ketonization. Lactonization followed by hydrolysis gives a cyclopentane with 3 or 4 well defined stereogenic centers.

O autorze

Martin Mwangi received a PhD from University of Iowa working on 'pot-in-pot' reactions. He is currently a Mary-Fieser postdoctoral fellow at Harvard University under the tutelage of Prof. George Whitesides. Martin's interests are in organic synthesis Methods, nano-, bioorganic, material and green chemistry.