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Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes

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

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Schreyer,  Lucas
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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Properzi,  Roberta
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

Kaib, P. S., Schreyer, L., Lee, S., Properzi, R., & List, B. (2016). Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes. Angewandte Chemie International Edition, 55(42), 13200-13203. doi:10.1002/anie.201607828.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002B-762C-6
Abstract
The enantioselective allylation of aldehydes to form homoallylic alcohols is one of the most frequently used carbon–carbon bond-forming reaction in chemical synthesis and, for several decades, has been a testing ground for new asymmetric methodology. However, a general and highly enantioselective catalytic addition of the inexpensive, nontoxic, air- and moisture-stable allyltrimethylsilane to aldehydes, the Hosomi–Sakurai[1] reaction, has remained elusive.[2, 3] Reported herein is the design and synthesis of a highly acidic imidodiphosphorimidate motif (IDPi), which enables this transformation, thus converting various aldehydes with aromatic and aliphatic groups at catalyst loadings ranging from 0.05 to 2.0 mol % with excellent enantioselectivities. Our rationally constructed catalysts feature a highly tunable active site, and selectively process small substrates, thus promising utility in various other challenging chemical reactions.