The influence of exocyclic stereochemistry on the tethered aminohydroxylation reaction.
نویسندگان
چکیده
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.
منابع مشابه
A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation.
A novel, practical and efficient enantioselective synthesis of sphingoid bases, l-threo-[2S,3S]-sphinganine (safingol), l-threo-[2S,3S]-sphingosine, l-arabino-[2R,3S,4R] and l-xylo-[2R,3S,4S]-C(18)-phytosphingosine is described. The synthetic strategy features the Sharpless kinetic resolution and tethered aminohydroxylation (TA) as the key steps.
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ورودعنوان ژورنال:
- Chemistry, an Asian journal
دوره 6 12 شماره
صفحات -
تاریخ انتشار 2011