137258-06-1Relevant academic research and scientific papers
The influence of exocyclic stereochemistry on the tethered aminohydroxylation reaction
Donohoe, Timothy J.,Lacy, Adam R.,Rathi, Akshat H.,Walter, Daryl S.
supporting information, p. 3214 - 3222 (2013/01/12)
A new strategy that employs an exocyclic stereocenter to effect diastereocontrol in the tethered aminohydroxylation (TA) reaction is applied to the stereoselective synthesis of a range of amino alcohols in good to excellent yields, and with anti selectivities of up to 20:1. The influence of the reaction conditions and substrate parameters on the level of diastereocontrol is described. Furthermore, an "inside alkoxy" model is employed to rationalize the sense and degree of stereoselectivity observed in these systems. TA for now: Tethered aminohydroxylation (TA) cyclic stereocontrol is possible in the catalytic TA reaction of acyclic systems that bear an exocyclic stereodirecting group. The influence of the alkene substitution pattern and the role of the protecting group on the allylic alcohol are both explored. A model is also presented to rationalize the observed trends in stereoselectivity.
