103260-93-1Relevant articles and documents
Desymmetrizing hydroformylation of diallylcarbinols with the aid of a planar-chiral, catalyst-directing group
Breit, Bernhard,Breuninger, Daniel
, p. 3930 - 3941 (2005)
The desymmetrizing hydroformylation of diallylcarbinols has been achieved by employing a planar-chiral, substrate-bound catalyst-directing group - the ortho-(diphenylphosphanyl)ferrocenylcarbonyl group (o-DPPF). The method allows the simultaneous construction of two stereogenic centers in a 1,3-relative position with high levels of stereocontrol. The diastereoselectivity was investigated as a function of substrate structure. Determination of the relative and absolute configuration of the product aldehydes (chemical derivatization and X-ray crystallographic studies), as well as the conditions for removal and recovery of the catalyst-directing o-DPPF group, are described. Furthermore, a model is suggested that rationalizes the experimentally observed stereochemical result based on the minimization of syn-pentane interactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Desymmetrizing hydroformylation with the aid of a planar chiral catalyst-directing group
Breit, Bernhard,Breuninger, Daniel
, p. 10244 - 10245 (2007/10/03)
Desymmetrizing hydroformylation of bisalkenyl- and bisallylcarbinols could be achieved employing a chiral substrate-bound catalyst-directing group (o-DPPF) with excellent levels of diastereotopic alkene face and diastereotopic alkene group discrimination to give bifunctionalized chiral aldehydes in enantiomerically pure form. Copyright
