Application of the Luche Reduction in Synthesis
What are some
advantages
and
disadvantages
to this special reduction in regards to other methods?
Advantages:
It is a selective reduction that reduces the carbonyl group instead of a double bond
This reduction can reduce sterically hindered ketones, including ketones on rings
Certain stereochemical outcomes can be selected for by manipulating the temperature of the reaction environment
The Luche can be used to synthesize interesting steroid derivatives, such as shark repellent!
Disadvantages:
NaBH4 is a highly dangerous reagent; it is toxic when inhaled (causes irritation of the upper respiratory tract and even difficulty of breathing) and it is highly reactive with moisture, causing fires that cannot be extinguished using a fire extinguisher. For these safety reasons, it must be used under a well ventilated hood away from any moisture.
CeCl3 is an irritant of the eyes, skin, and respiratory system, so maintain caution when handling it.
CeCl3 is not budget friendly; it costs about $15.00/g.
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