Chem 30CL- Lecture 1c - Lecture 1c Click to edit Master...

Click to edit Master subtitle style
8/6/11
Asymmetric synthesis
Lecture 1c

8/6/11

Hanson, J., J.Chem.Educ. 2001 , 78(9) , 1266 (including
supplemental material ).

Larrow, J.F., Jacobsen, E.N., Org. Synth. 1998 , 75 , 1.

Cepanec, I. et al., Synth. Commun . 2001 , 31(19) , 2913.


Flessner, T., Doye, S., J.Prakt.Chem. 1999 , 341 , 436.

McGarrigle, E.M., Gilheany, D.G., Chem.Rev. 2005 ,
105(5) , 1563.

Schurig, V., Nowotny, H.P., Angew.Chem. Int. Ed. Engl .
1990 , 29(9) , 939.
Assigned reading

8/6/11

Chirality plays important key role in many biological
systems

Many drugs are single enantiomer drugs because often
only one enantiomer is active in a desirable fashion while
the other enantiomer is harmful

Some of these drugs are isomerized in vivo (*)
Why asymmetric synthesis?
Drug R-form S-form
Thalidomide Morning
sickness
Teratogenic*
Ibuprofen Slow acting Fast acting*
Prozac Anti-
depressant
Helps against
migraine
N
O
O
*
NH
O
O
COOH

8/6/11
History of Asymmetric Synthesis I

1848 Louis Pasteur discovers
chirality

1912 Bredig and Fiske conduct first