. Author manuscript; available in PMC: 2020 May 7.

Published in final edited form as: J Org Chem. 2018 Dec 5;83(24):15449–15462. doi: 10.1021/acs.joc.8b02724

Table 5.

DFT-calculated (B3LYP-6–31g**) relative energies of pyrrolodiazepinone diastereomers arising from cyclization Pathway B from either L- or D-amino acid-derived substrates 1.


Entry	Starting Material	Relative energies^a for diastereomers of pyrrolodiazepinones 3 (kcal/mol)
Entry	Starting Material	(5S,9aS)	(5S,9aR)	(5R,9aR)	(5R,9aS)
1	1a	+0.4	+1.8	0	+1.2
2	1b	+0.5	+2.3	0	+2.5
3	1c	+0.5	+1.3	0	+0.9
4	1d	+0.3	+2.0	0	+1.2

^a)

Relative energies are reported as Gibbs free energy differences in kcal/mol and were calculated with Jaguar (Schrodinger, Inc.) on DFT-optimized (B3LYP/6–31G**) structures in the absence of solvent.