Download Lecture 1: Key Concepts in Stereoselective Synthesis

yes no Was this document useful for you?
   Thank you for your participation!

* Your assessment is very important for improving the work of artificial intelligence, which forms the content of this project

Document related concepts

Metalloprotein wikipedia, lookup

Evolution of metal ions in biological systems wikipedia, lookup

Coordination complex wikipedia, lookup

Hydroformylation wikipedia, lookup

Ring-closing metathesis wikipedia, lookup

Baylis–Hillman reaction wikipedia, lookup

Metal carbonyl wikipedia, lookup

Stability constants of complexes wikipedia, lookup

Fischer–Tropsch process wikipedia, lookup

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Update to 2012
Bode Research Group
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
3.6.1 Aldehyde as electrophiles