1. Mike Mulholland Literature Meeting October 23rd 2012
Regio- and Enantioselective Cobalt-Catalyzed Reductive [3+2] Cycloaddition Reaction of Alkynes with Cyclic Enones: A Route to Bicyclic Tertiary Alcohols Chu-Hung Wei, Subramaniyan Mannathan, and Chien-Hong Cheng
Mike Mulholland
Literature Meeting
October 23rd 2012

2. Cobalt Chemistry Group 9 II is most common oxidation state
I and III are well known from catalysis
High affinity for alkynes (eg. Nicholas reaction)

3. Catalytic Cobalt Catalyzed Reactions of Alkynes
The Pauson-Khand reaction
For a review of the basics see: Pauson, P. L. Tetrahedron 1985, 41, 5855.
Alkyne Cyclotrimerization
For a review about applications in synthesis see: Vollhardt, K. P. C.; Acc. Chem. Res., 1977, 10, 1.

4. Formation of Similar Motifs
Movassaghi, M.; Chen, B. Angew. Chem. Int. Ed. 2007, 46, 565.
Zi, W.; Yu, S.; Ma, D. Angew. Chem. Int. Ed. 2010, 49, 5887.

5. Natural Products

6. Reaction Overview Excess of alkene helps prevent alkyne homocoupling
Mn is terminal reductant
Net 2 electron reduction

7. Mechanism

8. Scope

9. Enantioselective Transformation

10. Rational for Selectivity