Chemoenzymatic Preparation of a Key Intermediate for Carbapenem Synthesis Starting from Asymmetrized Bis(hydroxymethyl)acetaldehyde (BHYMA)

Article abstract of DOI:10.1016/S0040-4020(01)87214-8

4-Unsubstituted 2-azetidinones 3a,b, which are useful intermediates for the synthesis of carbapenem abtibiotics, have been enantiospecifically and diastereoselectively prepared starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA) 4, a new chiral building block obtained through biological methods.The key steps are the highly diastereoselective addition of Me2CuLi to 4 (diast. ratio = 95 : 5), and the regioselective deblocking of tBuMe2Si ether in the presence of a (iPr)3Si ether, by using a novel methodology.