TY - JOUR
T1 - Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses
AU - Schober, Lukas
AU - Tonin, Fabio
AU - Hanefeld, Ulf
AU - Gröger, Harald
PY - 2022
Y1 - 2022
N2 - A sequential-type as well as a tandem-type chemoenzymatic flow cascade combining an organocatalytic aldol reaction and a biocatalytic reduction to form stereoselectively a 1,3-diol with two stereogenic centers were developed. Initially, a comprehensive screening of 24 alcohol dehydrogenases was carried out and the identified candidates were applied in different multi-step flow cascades. All four stereoisomers of the desired 1,3-diol product are accessible via a sequential flow approach with product formation-related conversions of up to 76 % over two steps, isolated yields of up to 64 % and enantiomeric excess of >99 % in all cases. In addition, a tandem-type flow process, performing both reaction steps simultaneously, was established leading to 51 % conversion with >99 % ee and 8 : 1 d.r. and representing a combination of the fields of asymmetric chemocatalysis, biocatalysis and flow chemistry.
AB - A sequential-type as well as a tandem-type chemoenzymatic flow cascade combining an organocatalytic aldol reaction and a biocatalytic reduction to form stereoselectively a 1,3-diol with two stereogenic centers were developed. Initially, a comprehensive screening of 24 alcohol dehydrogenases was carried out and the identified candidates were applied in different multi-step flow cascades. All four stereoisomers of the desired 1,3-diol product are accessible via a sequential flow approach with product formation-related conversions of up to 76 % over two steps, isolated yields of up to 64 % and enantiomeric excess of >99 % in all cases. In addition, a tandem-type flow process, performing both reaction steps simultaneously, was established leading to 51 % conversion with >99 % ee and 8 : 1 d.r. and representing a combination of the fields of asymmetric chemocatalysis, biocatalysis and flow chemistry.
KW - Asymmetric catalysis
KW - Biocatalysis
KW - Chemoenzymatic cascades
KW - Flow chemistry
KW - Organocatalysis
UR - http://www.scopus.com/inward/record.url?scp=85125131951&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202101035
DO - 10.1002/ejoc.202101035
M3 - Article
AN - SCOPUS:85125131951
SN - 1434-193X
VL - 2022
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 7
M1 - e202101035
ER -