Heteroatom Chemistry / 2019 / Article / Tab 1

Research Article

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.

EpoxideAmineProduct, yield (%)aTotal yield (%)

11(S)-1-Phenylethylamine(1S,2S,1′S)-21, 26 (1R,2R,1′S)-21, 2652
11(R)-1-Phenylethylamine(1R,2R,1′R)-21, 29 (1S,2S,1′R)-21, 2958
11(R)-1-Cyclohexylethylamine(1R,2R,1′R)-22, 33 (1S,2S,1′R)-22, 3366
12(S)-1-Phenylethylamine(1S,2S,1′S)-23, 30 (1R,2R,1′S)-23, 3060
12(R)-1-Cyclohexylethylamine(1R,2R,1′R)-24, 32 (1S,2S,1′R)-24b64
13b(R)-1-Phenylethylamine(1R,2R,1′R)-25, (1S,2S,1′R)-25c8

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.

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