Amprenavir, Henry reaction

The Henry reactions of A, ALdibenzyl-L-phenylalaninal with nitroalkanes using 1.2 equiv of tetrabutylammonium fluoride (TBAF) as the catalyst proceed in ahighly stereoselective manner, as shown in Eqs. 3.82 and 3.83. This reaction provides rapid and stereoselective access to important molecules containing 1,3-diamino-2-hydroxypropyl segments, which are cenhal structural subunit of the HIV protease inhibitor amprenavir (in Scheme 3.21). 

The key step of making Amprenavir 35, an HIV protease inhibitor successfully marketed by Vertex, involves asymmetric Henry reaction... 

SCHEME 4.23. Application of the Henry reaction to the synthesis of amprenavir. 

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