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Journal Article

Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates

MPS-Authors
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Schreyer,  Lucas
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Kaib,  Philip S.J.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wakchaure,  Vijay N.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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

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

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

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Citation

Schreyer, L., Kaib, P. S., Wakchaure, V. N., Obradors, C., Properzi, R., Lee, S., et al. (2018). Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates. Science, 362(6411), 216-219. doi:10.1126/science.aau0817.


Cite as: http://hdl.handle.net/21.11116/0000-0002-73D5-C
Abstract
Reactions that form a product with the same reactive functionality as that of one of the starting compounds frequently end in oligomerization. As a salient example, selective aldol coupling of the smallest, though arguably most useful, enolizable aldehyde, acetaldehyde, with just one partner substrate has proven to be extremely challenging. Here, we report a highly enantioselective Mukaiyama aldol reaction with the simple triethylsilyl (TES) and tert-butyldimethylsilyl (TBS) enolates of acetaldehyde and various aliphatic and aromatic acceptor aldehydes. The reaction is catalyzed by recently developed, strongly acidic imidodiphosphorimidates (IDPi), which, like enzymes, display a confined active site but, like small-molecule catalysts, have a broad substrate scope. The process is scalable, fast, efficient (0.5 to 1.5 mole % catalyst loading), and greatly simplifies access to highly valuable silylated acetaldehyde aldols.