Chiral α,β-Epoxy Group as a Stereocontrolling Element in the Reduction of N-Metalloimines. A Short Synthesis of anti-Epoxy Amines

Article abstract of DOI:10.1021/jo00045a006

Reduction of the α,β-epoxy N-metalloimines generated from the TBS ether of (2S,3S)-3-cyano-2,3-epoxy-1-propanol (1), Grignard reagents, and Me3SiCl with NaBH4 afforded the TBS ethers of (2S,3S,4S)-4-amino-2,3-epoxy-1-alkanols 4 with diastereoselectivities of up to 95:5.