A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442. https://doi.org/10.3762/bjoc.12.236

Supporting Information

Tables S1 to S4 (ladder patterns and generating sequences for determining the total number of unique 3- and 4-partitions of monocyclic rings); simple algorithms for enumerating the sets of unique 3- and 4-partitions of monocyclic rings; Schemes S1 to S3 showing [4 + 1 + 1], [3 + 2 + 1], and [2 + 2 + 2] coupling strategies to synthesize cyclohexanone; Figure S1 to S7 showing nucleophilic-electrophilic centre labels on 3-partition fragment possibilities for cyclohexanone, 2- and 3-partition fragment possibilities for piperidine, 2- and 3- partition fragment possibilities for cyclopentanone, and 2- and 3-partition fragment possibilities for pyrrolidine; Schemes S4 and S5 showing new [3 + 2 + 1] and [4 + 1 + 1] strategies to synthesize the Biginelli adduct; Schemes S6 to S32 showing superposition of 3-partition templates for various heterocycles.

Supporting Information File 1: Application of integer partitioning algorithm to monocyclic rings.
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Supporting Information File 2: Excel file of an MCR database of literature routes to various heterocycles.
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Supporting Information File 3: Excel file of statistics AE(min) and probability of intrinsic greenness for heterocyclic MCRs.
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