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• W2120685761 abstract "Abstract We present the first cyanohydrin derivative 4 that allows diastereoselective umpolung reactions. In 4 the OH group of the cyanohydrin is linked with a chiral phosphate, which can be removed hydrolytically after asymmetric synthesis. Cyclization of pseudoephedrine 1d with POCl 3 gave 2d . This was followed by addition of racemic benzaldehyde cyanohydrin 3 to give the key intermediate 4d with complete retention of the configuration at phosphorus. Deprotonation of 4d , followed by addition of a wide variety of electrophiles afforded the crystalline products 5 with high diastereomeric excesses ( de up to 94%). High asymmetric induction was also achieved for the reaction of 4 − Li + with acyl halides, α‐bromoacetates, 2‐cycloalkenones, α,β‐unsaturated esters, and γ‐bromoacetates. Lewis acid assisted hydrolysis proceeded without racemization and gave high yields of ketone cyanohydrins 6 . From the ring‐opened chiral auxiliary 7 , optically pure pseudoephedrine 1 was readily recovered by acid hydrolysis. Optically pure ( R ) and ( S ) ketone cyanohydrins are now accessible in a very general strategy, which circumvents the substrate limitations of enzymatic synthesis." @default.
• W2120685761 created "2016-06-24" @default.
• W2120685761 creator A5007187482 @default.
• W2120685761 date "1997-08-01" @default.
• W2120685761 modified "2023-10-17" @default.
• W2120685761 title "Stereoselective Umpolung Reactions with Metalated <i>P</i>‐Chiral Cyanohydrin Phosphates—Enantioselective Synthesis of Tertiary Cyanohydrins" @default.
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• W2120685761 doi "https://doi.org/10.1002/chem.19970030815" @default.
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