Nucleophilic Addition to (3-Methylpentadienyl)iron(1+) Cations: Counterion Control of Regioselectivity; Application to the Enantioselective Synthesis of 4,5-Disubstituted Cyclohexenones
作者:Subhabrata Chaudhury、William A. Donaldson
DOI:10.1021/ja055668y
日期:2006.5.1
regioselectivity of malonate addition to (3-methylpentadienyl)Fe(CO)3+ is controlled by the malonate-counterion association. The Li+ salt of malonate proceeds via C1 nucleophilic attack to afford the 1,3Z-diene complex 4a, while reaction of highly dissociated ion pair (i.e., Na+ or Li+/12-crown-4) salt proceeds at the C2 internal carbon to eventually afford cyclohexenone products 6. Reaction of 1a with
Synthetic studies directed toward the proposed structure for heteroscyphic acid A
作者:Subhabrata Chaudhury、Shukun Li、William A. Donaldson
DOI:10.1039/b602700h
日期:——
A route to the carbon skeleton of the proposedstructure for heteroscyphic acid A was developed utilizing a Mn(III)/Cu(II) mediated oxidative free-radical cyclization and nucleophilic addition to (3-methylpentadienyl)iron(1+) cation.