and these reactions tend to be versatile and very well-studied, allowing the most time-efficient access to enantiomerically pure products. Additionally, the products of auxiliary-directed reactions are diastereomers, which enables their facile separation by methods such as column chromatography or crystallization. Biocatalysis Biocatalysis makes use of biological compounds, ranging from isolated enzymes to living cells, to perform chemical transformations. The advantages of these reagents include very high e.e.s and reagent specificity, as well as mild operating conditions and low environmental impact. Biocatalysts are more commonly used in industry than in academic research; for example in the production of statins. The high reagent specificity can be a problem, however, as it often requires that a wide range of biocatalysts be screened before an effective reagent is found. Enantioselective organocatalysis Organocatalysis refers to a form of catalysis, where the rate of a chemical reaction is increased by an organic compound consisting of carbon, hydrogen, sulfur and other non-metal elements. When the organocatalyst is chiral, then enantioselective synthesis can be achieved; for example a number of carbon–carbon bond forming reactions become enantioselective in the presence of proline with the aldol reaction being a prime example. Organocatalysis often employs natural compounds and secondary amines as chiral catalysts; these are inexpensive and environmentally friendly, as no metals are involved. Chiral pool synthesis Chiral pool synthesis is one of the simplest and oldest approaches for enantioselective synthesis. A readily available chiral starting material is manipulated through successive reactions, often using achiral reagents, to obtain the desired target molecule. This can meet the criteria for enantioselective synthesis when a new chiral species is created, such as in an SN2 reaction. Chiral pool synthesis is especially attractive for target molecules having similar chirality to a relatively inexpensive naturally occurring building-block such as a sugar or amino acid. However, the number of possible reactions the molecule can undergo is restricted and tortuous synthetic routes may be required (e.g. Oseltamivir total synthesis). This approach also requires a stoichiometric amount of the enantiopure starting material, which can be expensive if it is not naturally occurring. Separation and analysis of enantiomers The two enantiomers of a molecule possess many of the same physical properties (e.g. melting point, boiling point, polarity etc.) and so behave identically to each other. As a result, they will migrate with an identical Rf in thin layer chromatography and have identical retention times in HPLC and GC. Their NMR