Lect17_0930 - HO HO NH 3 H CO 2 L-DOPA (treatment for...

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Ch. 5 - 1 An equimolar mixture of two enantiomers is called a racemic mixture (or racemate or racemic form) A racemic mixture causes no net rotation of plane-polarized light 9A. 9A. Racemic Racemic Forms Forms rotation equal & opposite rotation by the enantiomer
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Ch. 5 - 2 Enantiomeric excess (ee) Also known as the optical purity Can be calculated from optical rotations
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Ch. 5 - 3 10. The Synthesis of Chiral Molecules 10A. 10A. Racemic Racemic Forms Forms O CH 3 CH 2 CCH 3 HH ( )-CH 3 CH 2 CHCH 3 OH + Ni Butanone (achiral molecules) Hydrogen (achiral molecules) ( )-2-Butanol (chiral molecules; but 50:50 mixture
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Ch. 5 - 4
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Ch. 5 - 5 OEt O F OH O F + EtO H H + ,H 2 O heat racemate ( ) racemate ( ) OEt O F OH O F + EtO H H 2 O lipase racemate ( ) ( ) (> 69% ee) OEt O F (+) (> 99% ee) + 10B. 10B. Stereoselective Stereoselective Syntheses Syntheses Lipase has chiral centers
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Ch. 5 - 6 11. Chiral Drugs Of the $475 billion in world-wide sales of formulated pharmaceutical products in 2008, $205 billion was attributable to single enantiomer drugs O NMe 2 F NC Escitalpram (anti-depressant )
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Unformatted text preview: HO HO NH 3 H CO 2 L-DOPA (treatment for Parkinson's) Ch. 5 - 7 Singulair (asthma and allergy treatment) Naproxen (anti-inflammatory drug) MeO CH 3 CO 2 H N HO CH 3 CH 3 S NaO 2 C Cl Ch. 5 - 8 3 3 3 3 Note : In compounds with n tetrahedral stereocenters, the maximum number of stereoisomers is 2 . 12. Molecules with More than One Chirality Center Ch. 5 - 9 12 12 Meso Meso Compounds Compounds Compounds with two stereocenters do not always have four stereoisomers (2 2 = 4) since some molecules are achiral (not chiral), even though they contain stereocenters For example, 2,3-dichlorobutane has two stereocenters, but only has 3 stereoisomers (not 4) Ch. 5 - 10 13. Fischer Projection Formulas 13A. 13A. How To How To Draw and Use Fischer Draw and Use Fischer Projections Projections H 3 C Ph COOH HO Et Br Et OH Br Ph CH 3 COOH Et OH Br Ph CH 3 COOH Fischer Projection...
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Lect17_0930 - HO HO NH 3 H CO 2 L-DOPA (treatment for...

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