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

Kaib, P. S. J., 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.

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 Creators:
Kaib, Philip S. J.1, Author              
Schreyer, Lucas1, Author              
Lee, Sunggi1, Author              
Properzi, Roberta1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: allylic compounds; enantioselectivity; nucleophilic addition: organocatalysis; silanes
 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.

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Language(s): eng - English
 Dates: 2016-08-112016-10-062016-10-10
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201607828
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 55 (42) Sequence Number: - Start / End Page: 13200 - 13203 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851