1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS

The development of organometallic-type reactions in aqueous media is r eviewed. Coupling reactions of allyl halides with carbonyl compounds m ediated by zinc, or tin, or indium in aqueous media to give homoallyli c alcohols are discussed. The stereochemical outcome is compared with similar reactions in organic solvents. A concise synthesis of (+)-musc arine is used to illustrate the usefulness of aqueous organometallic-t ype reactions in organic synthesis. The procedure to protect-deprotect hydroxy functional groups may not be necessary in these reactions. An application in the carbohydrate area is demonstrated with the synthes is of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). The mech anistic possibilities of organometallic-type reactions in aqueous medi a are outlined.