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Improved Methodology for the Preparation of Chiral Amines

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compared to <strong>the</strong> oil refinery industry which has <strong>the</strong> lowest E factor. Atom efficiency is<br />

calculated by dividing <strong>the</strong> molecular weight <strong>of</strong> <strong>the</strong> desired product by <strong>the</strong> sum <strong>of</strong> <strong>the</strong><br />

molecular weights <strong>of</strong> all <strong>the</strong> substances produced in <strong>the</strong> stoichiometric equation.<br />

3.4.2. Hydrogenation and Green Chemistry:<br />

Catalytic hydrogenation–utilizing hydrogen gas and heterogeneous catalysts–can be<br />

considered as <strong>the</strong> most important catalytic method in syn<strong>the</strong>tic organic chemistry on both<br />

laboratory and production scales. Hydrogen is, without doubt, <strong>the</strong> cleanest reducing agent and<br />

<strong>the</strong> heterogeneous robust catalysts have been routinely employed. Catalytic hydrogenation<br />

has distinctive advantages over o<strong>the</strong>r methodologies. Key advantages <strong>of</strong> this technique are: [67]<br />

1. Broad scope, many functional groups can be hydrogenated with high selectivity.<br />

2. High conversions are usually obtained under relatively mild conditions in <strong>the</strong> liquid phase.<br />

3. The large body <strong>of</strong> experience with this technique makes it possible to predict <strong>the</strong> catalyst<br />

<strong>of</strong> choice <strong>for</strong> a particular problem.<br />

4. The process technology is well established and scale-up is <strong>the</strong>re<strong>for</strong>e usually<br />

straight<strong>for</strong>ward.<br />

The field <strong>of</strong> hydrogenation is also <strong>the</strong> area where catalysis was first widely applied in <strong>the</strong> fine<br />

chemical industry. It is a key example <strong>of</strong> green technology, due to <strong>the</strong> low amounts <strong>of</strong><br />

catalysts required, in combination with <strong>the</strong> use <strong>of</strong> hydrogen (100% atom efficient!) as <strong>the</strong><br />

reductant. In general, if chirality is not required, heterogeneous supported catalysts can be<br />

used in combination with hydrogen. Catalytic hydrogenation is considered as <strong>the</strong> green route<br />

<strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis <strong>of</strong> different functional compounds as amines, alcohols, and amino acids.<br />

Once selectivity and chirality is called <strong>for</strong>, homogeneous catalysts and biocatalysts are<br />

applied. The use and <strong>the</strong> application <strong>of</strong> chiral Ru, Rh and Ir catalysts has become a well<br />

developed technology. Homogenous catalytic hydrogenation gives access to a large variety <strong>of</strong><br />

asymmetric trans<strong>for</strong>mations: imines and functionalized ketones and alkenes can be converted<br />

with high selectivity in most cases.<br />

75

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