Rhodium-catalyzed and zinc(II)-triflate-promoted asymmetric hydrogenation of tetrasubstituted α,β-unsaturated ketones

Organic Letters

Volumn 14, Issue 4, 2012, Pages 1038-1041

  Calvin, Joel R ^a   Frederick, Michael O ^a   Laird, Dana L T ^a   Remacle, Jacob R ^a,b   May, Scott A ^a  

^a ELI LILLY AND COMPANY   (United States)

^b DOW CORNING CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; LIGAND; MESYLIC ACID DERIVATIVE; RHODIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; STEREOISOMERISM;

CATALYSIS; HYDROGENATION; KETONES; LIGANDS; MESYLATES; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 84857225359     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol203264a     Document Type: Article

References (25)

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24. 2 concentration by 20× should result in higher TfOH concentration. This, in turn, should result in an increased amount of product epimerization. We would also expect the hydrolysis rate of zinc triflate to be negligible on the basis of literature precedent. See: Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24, 169
25. See: May, S. A.; Johnson, M. D.; Braden, T. M.; Calvin, J. R.; Haeberle, B. D.; Jines, A. R.; Miller, R. D.; Rener, G. A.; Richey, R. N.; Schmid, C. R.; Vaid, R. K.; Yu., H. Org. Process Res. Dev. (submitted) for a full account of the scale up to 140 kg (88% yield) using a continuous process in a plug flow reactor.