Enzymatic resolution of chroman-4-ol and its core analogues with Burkholderia cepacia lipase

A convenient protocol for lipase resolution of chroman-4-ol and its analogues (six- and seven-membered rings with O, S, SO2) has been elaborated. The structure of substrates has minor influence on the efficiency of resolution.

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(4S)-Chroman-4-olC9H10O2[α]D20=-56.0 (c 1.38, EtOH), ee = 94%Absolute configuration: (4S)Source of chirality: Burkholderia cepacia lipase resolution

(5S)-2,3,4,5-Tetrahydro-1-benzoxepin-5-olC10H12O2[α]D20=-18.4 (c 0.7, CHCl3), ee = 99%Absolute configuration: (5S)Source of chirality: Burkholderia cepacia lipase resolution

(4S)-Thiochroman-4-olC9H10OS[α]D20=-104.5 (c 1.48, CHCl3), ee = 95%Absolute configuration: (4S)Source of chirality: Burkholderia cepacia lipase resolution

(5S)-2,3,4,5-Tetrahydro-1-benzothiepin-5-olC10H12OS[α]D20=-98.1 (c 3.2, EtOH), ee = 99%Absolute configuration: (5S)Source of chirality: Burkholderia cepacia lipase resolution

(4S)-1,1-Dioxo-3,4-dihydro-2H-thiochromen-4-olC9H10O3S[α]D20=+5.1 (c 1.41, CHCl3), ee = 95%Absolute configuration: (4S)Source of chirality: Burkholderia cepacia lipase resolution

(5S)-1,1-Dioxo-2,3,4,5-tetrahydro-1-benzothiepin-5-olC10H12O3S[α]D20=-32.8 (c 1.44, CHCl3), ee = 99%Absolute configuration: (5S)Source of chirality: Burkholderia cepacia lipase resolution