Abstract
The ethylation of 2-( N , N -dimethylaminomethyl)ferrocenylcarboxaldehyde 1 without a catalyst is stereospecific and occurs with high rates, yields and diastereoselectivities through an intramolecular asymmetric autoactivation. This reaction allowed the synthesis of the enantiopure (+)-( S ,1 S )-{2-( N , N -dimethyl-aminomethyl)ferrocenyl}-1-propanol 2 by applying this result to the enantiomerically pure aldehyde 1 . This new chiral auxiliary acted as a catalyst during the ethylation of benzaldehyde with diethylzinc. Without catalyst, the addition of Et 2 Zn to 1 led to 2 with 98% yield and more than 98% ee through an asymmetric intramolecular autoactivation.
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