Investigation of the rh-catalyzed asymmetric reductive aldol reaction. Expanded scope based on reaction analysis.
[reaction: see text] A series of experiments are described that suggest that the Rh-catalyzed reductive aldol reaction proceeds by addition of a Rh(I) hydride, generated in situ, to the reacting acrylate followed by a stereochemistry-controlling aldol addition reaction. On the basis of this hypothesis, reaction conditions are engineered that allow for increased substrate scope.
Russell
Albert E
AE
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Fuller
Nathan O
NO
Taylor
Steven J
SJ
Aurriset
Pauline
P
Morken
James P
JP
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D007202:Indicators and Reagents; D007659:Ketones; D012238:Rhodium