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Lewis Base-Bronsted Acid-Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses.

ABSTRACT: Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase; alcohol dehydrogenase): A gram-scale access to a variety of enantiopure key building blocks for natural product syntheses was enabled utilizing up to six catalytic steps within the same reaction vessel.

SUBMITTER: Mantel M

PROVIDER: S-EPMC8360128 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Lewis Base-Brønsted Acid-Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses.

Mantel Marvin M Giesler Markus M Guder Marian M Rüthlein Elisabeth E Hartmann Laura L Pietruszka Jörg J

Angewandte Chemie (International ed. in English) 20210501 30

Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase ...[more]

PMID: 33856095

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