Asymmertic Synthesis of β‐Azido Esters through a Combination of Aldol and Mitsunobu Reactions

Abstract This method offers several advantages over traditional methods for the asymmetric synthesis of β ‐azido esters. First, the use of N ‐acetyl camphorsultam allows for excellent stereoselectivity in the aldol reaction, which is crucial for the subsequent Mitsunobu reaction. Second, the use of trimethylsilyl azide (TMSN 3 ) instead of hydrazoic acid (HN 3 ) eliminates the need for handling a highly toxic and explosive reagent, making the process safer and easier to carry out. Third, the use of basic conditions for the Mitsunobu reaction allows for the reaction to proceed efficiently without the formation of the undesired silyl ethers.