Remote Diastereoselective Control via Organoiron Methodology: Stereoselective Preparation of 4,6-, 5,7- and 6,8-dien-2-ol (tricarbonyl) Iron Complexes

Authors

Peter Thomas Bell, Marquette UniversityFollow
Bireshwar Dasgupta, Marquette University
William Donaldson, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

6-20-1997

Publisher

Elsevier

Source Publication

Journal of Organometallic Chemistry

Source ISSN

0022-328X

Abstract

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.

Comments

Journal of Organometallic Chemistry, Vol. 58, No. 1-2 (June 20, 1997): 75-82. DOI.

Recommended Citation

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.
https://epublications.marquette.edu/chem_fac/835