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1 Stereoselective Reactions of Carbon—Carbon Double Bonds

DOI: 10.1055/sos-SD-201-00001

de Vries, J. G.Science of Synthesis: Stereoselective Synthesis, (201111.

It must have been around 1980. I was living in the Boston area doing a postdoc at Brandeis University after obtaining a Ph.D. in The Netherlands on asymmetric ketone reductions using a chiral dihydropyridine. Back then we called it bio-mimetic chemistry; the word organocatalysis had yet to be invented. The occasion was a visit of Ryoji Noyori to MIT where Barry Sharpless was his host. The latter had just invented the titanium-catalyzed asymmetric epoxidation of allylic alcohols and Noyori gave a brilliant lecture on the asymmetric reduction of aromatic ketones using a combination of lithium aluminum hydride and BINOL at 100°C. RutheniumBINAP was still in the making. The packed lecture room was boiling with excitement; we all knew that this was a historic moment. Thirty years later, it may be hard to imagine what the excitement was about. Not many people realize that as little as thirty years ago there simply was no catalytic method to obtain a chiral alcohol with high enantioselectivity, and there was no catalytic method to obtain an epoxide with high enantioselectivity. These were inconceivable breakthroughs at the time.

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