Enantio- and diastereoselective synthesis of (protected) 2-formyl- and 2-(hydroxymethyl)-1-phenylalkane-1,3-diols from chiral 2-methoxy-3-tosyl-1,3-oxazolidines by subsequent asymmetric formylation and aldolization

Trimethylsilyl enol ethers are successively converted into chirally protect ed alpha-formyl ketones by asymmetric formylation with the 2-methoxy-1,3-ox azolidine 2, transformed into the corresponding, thermodynamically determin ed (Z)-TMS enol ethers, and then are allowed to condense with aldehydes. Al l steps proceed with high stereoselectivity. Some synthetic options, arisin gs from the three differentiated oxygen functionalities in the intermediate s 8 are illustrated for the title target compounds.