Synthesis and structural investigation of the cyclochiral boron resorcinarenes obtained from l-amino acids and phenylboronic acid

A diastereoselective synthesis and structural investigation of novel boron derivatives of resorcinarenes from l-amino acids and phenylboronic acid is described.

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Resorcinarene derivative from phenylboronic acid and l-isoleucineC76H104O16N4B4[α]D25=+42.8 (c 0.32, CH3OH)Source of chirality: l-isoleucineAbsolute configuration: in-(P,S,S,RN,SB)

Resorcinarene derivative from phenylboronic acid and l-isoleucineC76H104O16N4B4[α]D25=-52.0 (c 0.32, CH3OH)Source of chirality: l-isoleucineAbsolute configuration: out-(M,S,R,RN,SB)

Resorcinarene derivative from phenylboronic acid and l-leucineC72H96O16N4B4[α]D25=-1.7 (c 0.35, CH3OH)Source of chirality: l-leucineAbsolute configuration: in-(P,S,S,RN,SB)

Resorcinarene derivative from phenylboronic acid and l-leucineC72H96O16N4B4[α]D25=-65.0 (c 0.18, CH3OH)Source of chirality: l-leucineAbsolute configuration: out-(M,S,R,RN,SB)

Resorcinarene derivative from phenylboronic acid and l-phenylalanineC84H88O16N4B4[α]D25=-7.0 (c 0.28, CH3COCH3)Source of chirality: l-phenylalanineAbsolute configuration: in-(P,S,S,RN,SB)

Resorcinarene derivative from phenylboronic acid and l-phenylalanineC84H88O16N4B4[α]D25=-65.5 (c 0.54, CH3OH)Source of chirality: l-phenylalanineAbsolute configuration: out-(M,S,R,RN,SB)

Resorcinarene derivative from phenylboronic acid and l-valineC68H88O16N4B4[α]D25=+33.0 (c 0.25, CH3OH)Source of chirality: l-valineAbsolute configuration: in-(P,S,S,RN,SB)

Resorcinarene derivative from phenylboronic acid and l-valineC68H88O16N4B4[α]D25=-43.0 (c 0.20, CH3OH)Source of chirality: l-valineAbsolute configuration: out-(M,S,R,RN,SB)