2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands

Table 1

Ring opening of 2-oxiranyl-azaarenes with chiral amines.

Epoxide	Amine	Product, yield (%)^a	Total yield (%)
11	(S)-1-Phenylethylamine	(1S,2S,1′S)-21, 26 (1R,2R,1′S)-21, 26	52
11	(R)-1-Phenylethylamine	(1R,2R,1′R)-21, 29 (1S,2S,1′R)-21, 29	58
11	(R)-1-Cyclohexylethylamine	(1R,2R,1′R)-22, 33 (1S,2S,1′R)-22, 33	66
12	(S)-1-Phenylethylamine	(1S,2S,1′S)-23, 30 (1R,2R,1′S)-23, 30	60
12	(R)-1-Cyclohexylethylamine	(1R,2R,1′R)-24, 32 (1S,2S,1′R)-24^b	64
13b	(R)-1-Phenylethylamine	(1R,2R,1′R)-25, (1S,2S,1′R)-25^c	8

^aThe yield of each isolated diastereomer. ^bPure (1S,2S,1′R)-24 could not be isolated (remained in a mixture). ^cThe isolated 1 : 1 diastereomeric mixture was identified by HR-MS and ¹H NMR.