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/
Eder ACIE 1971, 83, 496; Hajos JOC 1974, 39, 1615
Pioneering findings by List, Barbas III: Proline-catalyzed enantioselective intermolecular aldol addition
Barbas III JACS 2000, 122, 2395
3.5.1 Mechanism of proline-catalyzed aldol addition
Different proposed mechanisms and models for transition state
Discussion on mechanism:
Limitations of Proline-catalyzed aldol addition
- Relatively large amount of proline (20-30mol%)
- Large amount of ketones
- Low enantioselectivity with aromatic aldehydes
Houk ACIE 2004, 43, 5766
List PNAS 2004, 101, 5839
Blackmond BMCL 2009, 19, 3934
Trost Chem. Soc. Rev. 2010, 39, 1600
3.6
Progress
3.6.1 Aldehyde as electrophiles
17