Fig. 5: Applications of catalysts (S)-Cat-1 and (S)-Cat-2 in synthesis of enantiomerically enriched molecules. | Nature Communications

Fig. 5: Applications of catalysts (S)-Cat-1 and (S)-Cat-2 in synthesis of enantiomerically enriched molecules.

From: Reaction blueprints and logical control flow for parallelized chiral synthesis in the Chemputer

Fig. 5

α-functionalization of aldehydes via enamine intermediates (en) affords Michael addition products 1a,b and α-chlorinated 2. Functionalization of unsaturated aldehydes (3) via imininium intermediates (im) affords epoxidation product 4, decarboxalytive Michael addition product 5, Henry product 6, and double Henry-aldol domino cascade products 7a,b. Longer cascade sequences utilizing in situ derivatization of epoxidation product allows rapid construction of complex scaffolds such as 8 with multiple stereogenic centers in a fully automated synthetic procedure. MVK methyl vinyl ketone, NCS N-chlorosuccinimide, DBU 1,8-diazabicyclo[5.4.0]undec-7-ene.

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