Issue 3, 2014

Highly selective 4-alkynoic acids synthesis via iron-mediated complete inversion of stereogenic carbon centers

Abstract

An Fe-catalyzed highly regio- and diastereoselective reaction of 4-ethynyloxetan-2-ones with different Grignard reagents affording alkynes 3 in good yields with absolute configuration of the β-carbon atom completely inverted has been developed. The optically active acids may be easily converted to esters, which may easily undergo desilylation and highly diastereoselective allenylation to afford optically active 4,5-allenoates with two chiral centers and one axial allene chirality.

Graphical abstract: Highly selective 4-alkynoic acids synthesis via iron-mediated complete inversion of stereogenic carbon centers

Supplementary files

Article information

Article type
Research Article
Submitted
11 Kax 2013
Accepted
07 Qun 2014
First published
19 Nah 2014

Org. Chem. Front., 2014,1, 247-252

Highly selective 4-alkynoic acids synthesis via iron-mediated complete inversion of stereogenic carbon centers

X. Zhang, Y. Qiu, C. Fu and S. Ma, Org. Chem. Front., 2014, 1, 247 DOI: 10.1039/C3QO00066D

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