Remote Diastereoselective Control via Organoiron Methodology: Stereoselective Preparation of 4,6-, 5,7- and 6,8-dien-2-ol (tricarbonyl) Iron Complexes
Journal of Organometallic Chemistry
The diastereoselective preparation of 2,3-, 2,4- and 2,5-diol iron complexes was accomplished in the following fashion: (2,4,6-octatriene)Fe(CO)3undergoes diastereoselective osmylation to provide (4,6-octadien-2,3-diol)Fe(CO)3; (4-hydroxy-5,7-nonadien-2-one)Fe(CO)3 may be reduced in a diastereoselective fashion to give mixtures predominating in either the syn- or anti-(5,7-nonadien-2,4-diol)Fe(CO)3; and diastereospecific addition of MeTi(OiPr)3 to the lactol of (5-hydroxy-6,8-decadienal)Fe(CO)3 gives (6,8-decadien-2,5-diol)Fe(CO)3. In each of the cases noted above, the hydroxyl group adjacent to the (diene)Fe(CO)3 group may be removed via ionic hydrogenation. The ionization of this hydroxyl is rationalized on the basis of the intermediacy of a transoid (pentadienyl)Fe(CO)3 cation species.
Bell, Peter Thomas; Dasgupta, Bireshwar; and Donaldson, William, "Remote Diastereoselective Control via Organoiron Methodology: Stereoselective Preparation of 4,6-, 5,7- and 6,8-dien-2-ol (tricarbonyl) Iron Complexes" (1997). Chemistry Faculty Research and Publications. 835.