Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine

We present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of aziridines with pendant silanols is compatible with a range of substrates. To engage productively in ring opening, the aziridine must be at least mildly activated, and a variety of such N-substituents are tolerated. The utility of this methodology is highlighted in facile preparations of the natural products (+/-)-Clavaminol H, (+/-)-dihydrosphingosine, and (+/-)-N-hexanoyldihydrosphingosine as well as a natural product analogue (+/-)-des-acetyl-Clavaminol H.

Automated summary

We present a unique strategy for the synthesis of vicinal amino alcohols through ring opening of aziridines with pendant silanols, which is compatible with a range of substrates. This method requires mild activation of the aziridine and tolerates various N-substituents. It has been successfully applied in the facile preparation of natural products and analogues.