Dynamic Diastereoselectivity during Iron Carbonyl Mediated
Spirocyclization Reactions
Anthony J. Pearson
Huikai Sun
Xiaolong Wang
10.1021/jo0625608.s001
https://acs.figshare.com/articles/journal_contribution/Dynamic_Diastereoselectivity_during_Iron_Carbonyl_Mediated_Spirocyclization_Reactions/3016012
Dynamic diastereoselectivity during Fe(CO)<sub>3</sub> promoted [6 + 2] ene spirocyclization of <b>35a</b> and <b>35b</b>,
having a chiral center on the pendent side chain, was investigated and gave rise to products <b>28a</b> and <b>28b</b>
instead of four possible isomers. From this reaction, two chiral centers are generated, with absolute
stereochemistry determined by the double bond geometry and the chiral center already present. <b>28a</b>/<b>b</b>
and the diene product from demetallation of <b>28a</b> are proposed as potential intermediates for total synthesis
of 18-deoxycytochalasin H. Furthermore, a stepwise second cyclization and a tandem double cyclization
mediated by the Fe(CO)<sub>3</sub> moiety was investigated.
2007-03-30 00:00:00
chiral center
Fe
Iron Carbonyl Mediated Spirocyclization ReactionsDynamic diastereoselectivity
pendent side chain