Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: aspects on the preparation and enantiopreference

The preparative scale kinetic resolution of racemic ethyl 2- and 3-furyl- and 2- and 3-thienyl-3-hydroxypropanoates has been performed by Candida antarctica lipases A and B with vinyl esters. A study based on the present work together with the literature has been carried out in terms of lipase enantiopreference and substrate structure. We also discuss the excellent behavior of the lipase A in O-acylations of secondary alcohols with respect to enantiopreference.

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(S)-Ethyl 3-hydroxy-3-(thiophen-2-yl)propanoateC9H12O3SEe = 99%[α]D20=-17 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (S)

(S)-Ethyl 3-(furan-2-yl)-3-hydroxypropanoateC9H12O4Ee = 99%[α]D20=-16 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (S)

(S)-Ethyl 3-(furan-3-yl)-3-hydroxy-propanoateC9H12O3SEe = 99%[α]D20=-44 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (S)

(S)-Ethyl 3-(furan-3-yl)-3-hydroxy-propanoateC9H12O4Ee = 97%[α]D20=-29 (c 1.0, CHCl3)Source of chirality: Enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (S)

(R)-3-Ethoxy-3-oxo-1-(thiophen-2-yl)propyl butyrateC13H18O4SEe = 96%[α]D20=+88 (c 1.0, CHCl3)Source of chirality: Enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (R)

(R)-3-Ethoxy-1-(furan-2-yl)-3-oxopropyl butyrateC13H18O5Ee = 97%[α]D20=+85 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (R)

(R)-3-Ethoxy-3-oxo-1-(thiophen-3-yl)propyl butyrateC13H18O4SEe = 99%[α]D20=+49 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (R)

(R)-3-Ethoxy-1-(furan-3-yl)-3-oxopropyl butyrateC13H18O5Ee = 99%[α]D20=+52 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase B from Candida antarcticaAbsolute configuration: (R)

(S)-Ethyl 3-acetoxy-3-(thiophen-2-yl)propanoateC11H14O4SEe = 94%[α]D20=-63 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase A from Candida antarcticaAbsolute configuration: (S)

(S)-Ethyl 3-acetoxy-3-(furan-2-yl)propanoateC11H14O5Ee = 90%[α]D20=-60 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase A from Candida antarcticaAbsolute configuration: (S)

(S)-Ethyl 3-acetoxy-3-(thiophen-3-yl)propanoateC11H14O4SEe = 81%[α]D20=-47 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase A from Candida antarcticaAbsolute configuration: (S)

(S)-Ethyl 3-acetoxy-3-(furan-3-yl)propanoateC11H14O5Ee = 88%[α]D20=-58 (c 1.0, CHCl3)Source of chirality: enzymatic resolution by lipase A from Candida antarcticaAbsolute configuration: (S)