Axially-unfixed　2,2　＇-bipyridine-based　chiral　catalysts　were　synthesized　using　enantiopure　amino　acids　as　chiral　sources,　which　were　successfully　used　in　asymmetric　aldol　reactions　ofp-nitrobenzaldehyde　with　cyclohexanone,　while　the　bulkier　aldehyde　derivatives　(2-naphthaldehyde,　9-anthracenecarboxaldehyde,　and　1-pyrenecarboxaldehyde)　were　selected　to　further　elucidate　the　catalytic　properties.　Particularly,　the　influences　of　the　bipyridine-proline　chiral　structures　and　the　polarities　of　used　solvents　(petroleum　ether,　toluene,　CH2Cl2,　ethanol,　DMF,　DMSO,　and　water)　on　the　catalytic　performance　were　investigated.　The　results　indicated　that　the　structure　of　bipyridine　catalysts,　the　molecular　volume　of　aldehydes,　and　the　polarity　of　solvents　have　significant　effects　on　the　catalytic　activities,　in　which,　the　smaller　steric　effects　were　conducive　to　the　improvement　of　the　yields　and　stereoselectivities　for　asymmetric　aldol　reaction,　along　with　the　increased　polarity　of　used　solvents　and　the　decreased　molecular　volume　of　aldehydes.　Meanwhile,　the　chemical　identity　of　all　compounds　was　confirmed　by(1)H-NMR,C-13-NMR,　HRMS,　and　HPLC　analysis.