1,3-Dipolar cycloaddition of azomethine ylides and dipolarophiles represents an effective approach for synthesizing diverse N and S-heterocyclic compounds.1 Over the past decades, utilization of thiazolium and benzothiazolium azomethine ylides have been particularly prominent in the synthesis of heterocyclic compounds with multiple stereogenic centers via 1,3-dipolar cycloadditions in racemic form.2 However, the enantioselective synthesis of chiral heterocyclic compounds and their derivatives are yet to be addressed with this framework. Our research endeavors to address this gap by developing a methodology for synthesizing chiral heterocyclic compounds containing multiple stereogenic centers, via 1,3-dipolar cycloaddition/rearrangement/ring-opening/ring-cleavage sequence. This work encompasses results including organocatalyzed (i) domino enantio- and diastereoselective synthesis of pyrrolo-thiazine-2-carbaldehydes; (ii) one-pot enantioselective synthesis of tetrasubstituted dihydropyrrole-3-carbaldehydes;3 (iii) domino synthesis of trisubstituted-1H-pyrrole-3-carbaldehydes; and (iv) domino enantioselective synthesis of chiral trisubstituted dihydro-1H-pyrrole-3-carbaldehydes4 in Scheme 1.

Scheme 1. Enantioselective synthesis of chiral heterocyclic compounds
References:
1. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765-2810.
2. Sahoo, C. S.; Joshi, M.; Pan, S. C. J. Org. Chem. 2017, 82, 12763-12770.
3. Pandidurai, S.; Choutipalli, V. S. K.; Subramanian, V.; Sekar, G. ChemRxiv 2023.
4. Pandidurai, S.; Sekar, G (Manuscript under preparation).