Chemistry and Industry, May 19th, 2003
Miller, Huang and Jamison at Massachusetts Institute of Technology (MIT) have developed a route to couple aldehydes to alkynes to give allylic alcohols with high levels of enantioselectivities (J Am Chem Soc 2003, 125, 3442), The reaction gives highest yields and regioselectivities when the alkyne is aryl substituted. A menthol-derived phosphine. NMDPP, on nickel, that has been known for some time but not widely used, was applied to give the optimal results. Reaction 1 shows a typical transformation and intermediate A is the one thought to be involved in the enantio-determinant step. The pract...
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