Nitrated Confined Imidodiphosphates Enable a Catalytic Asymmetric 
Oxa-Pictet–Spengler Reaction

Das, Sayantani; Liu, Luping; Zheng, Yiying; Alachraf, Mohammed Wasim; Thiel, Walter; De, Chandra Kanta; List, Benjamin

doi:10.1021/jacs.6b06626

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Nitrated Confined Imidodiphosphates Enable a Catalytic Asymmetric Oxa-Pictet–Spengler Reaction

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Das, Sayantani
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons180741

Liu, Luping
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons186078

Zheng, Yiying
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58388

Alachraf, Mohammed Wasim
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons59045

Thiel, Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons132969

De, Chandra Kanta
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58764

List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Das, S., Liu, L., Zheng, Y., Alachraf, M. W., Thiel, W., De, C. K., et al. (2016). Nitrated Confined Imidodiphosphates Enable a Catalytic Asymmetric Oxa-Pictet–Spengler Reaction. Journal of the American Chemical Society, 138(30), 9429-9432. doi:10.1021/jacs.6b06626.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-196C-2

Abstract

The development of a highly enantioselective catalytic oxa-Pictet–Spengler reaction has proven a great challenge for chemical synthesis. We now report the first example of such a process, which was realized by utilizing a nitrated confined imidodiphosphoric acid catalyst. Our approach provides substituted isochroman derivatives from both aliphatic and aromatic aldehydes with high yields and excellent enantioselectivities. DFT calculations provide insight into the reaction mechanism.