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Combinatorial Ligand Assisted Simultaneous Control of Axial and Central Chirality in Highly Stereoselective C−H Allylation

https://doi.org/10.1002/anie.202310112

Bhattacharya, Trisha; Ghosh, Supratim; Dutta, Subhabrata; Guin, Srimanta; Ghosh, Animesh; Ge, Haibo; Sunoj, Raghavan B; Maiti, Debabrata (January 2024, Angewandte Chemie International Edition)

Abstract The significance of stereoselective C−H bond functionalization thrives on its direct application potential to pharmaceuticals or complex chiral molecule synthesis. Complication arises when there are multiple stereogenic elements such as a center and an axis of chirality to control. Over the years cooperative assistance of multiple chiral ligands has been applied to control only chiral centers. In this work, we harness the essence of cooperative ligand approach to control two different stereogenic elements in the same molecule by atroposelective allylation to synthesize axially chiral biaryls from its racemic precursor. The crucial roles played by chiral phosphoric acid and chiral amino acid ligand in concert helped us to obtain one major stereoisomer out of four distinct possibilities.
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Double Strain-Release [2π+2σ]-Photocycloaddition

https://doi.org/10.1021/jacs.3c11563

Dutta, Subhabrata; Lu, Yi-Lin; Erchinger, Johannes E; Shao, Huiling; Studer, Emanuel; Schäfer, Felix; Wang, Huamin; Rana, Debanjan; Daniliuc, Constantin G; Houk, K N; et al (February 2024, Journal of the American Chemical Society)

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Dearomative ring expansion of thiophenes by bicyclobutane insertion

https://doi.org/10.1126/science.adh9737

Wang, Huamin; Shao, Huiling; Das, Ankita; Dutta, Subhabrata; Chan, Hok Tsun; Daniliuc, Constantin; Houk, K. N.; Glorius, Frank (July 2023, Science)

Skeletal ring enlargement is gaining renewed interest in synthetic chemistry and has recently focused on insertion of one or two atoms. Strategies for heterocyclic expansion through small-ring insertion remain elusive, although they would lead to the efficient formation of bicyclic products. Here, we report a photoinduced dearomative ring enlargement of thiophenes by insertion of bicyclo[1.1.0]butanes to produce eight-membered bicyclic rings under mild conditions. The synthetic value, broad functional-group compatibility, and excellent chemo- and regioselectivity were demonstrated by scope evaluation and product derivatization. Experimental and computational studies point toward a photoredox-induced radical pathway.
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