Download Lecture 1: Key Concepts in Stereoselective Synthesis

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Transcript
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Update to 2012
Bode Research Group
http://www.bode.ethz.ch/
- Complex of Ti(IV), tridentate Schiff base and di tert-butylsalicylic acid by Carreira
Carreira JACS 1994, 116, 8837
Carreira, Kvaerno Classics in stereoselective synthesis p.133-134
- Complex of chiral Cu(II)-Pyridine Bis(Oxazoline) (PyBOX) complex by Evans
Evans JACS 2000, 122, 10033; ACIE 1997, 36, 2744
3.2.4.4 Ketones as electrophiles
- Evans developed a family of chiral BOX complexs with different metals as catalysts for enantioselective
Mukaiyama aldol reactions.
Bidentate chelation leads to the formation of a square pyramidal complex and the re aldehyde enantioface is
shielded -> High level of diastereoselectivity and enantioselectivity.
The requirement of chelation limits the scope of electrophiles (-alkoxyacetaldehydes, pyruvates, glycolates,
-diketones, 5-formyloxazoles).
Chiral Cu(II)/tert-Bu-BOX complex
Evans JACS 1997, 119, 7893
Chiral Sn(II)/Ph-PyBOX complex
12