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  Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates

Schreyer, L., Kaib, P. S. J., 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.

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Schreyer, Kaib, Wakchaure, Obradors, Properzi, Lee, List 2018.pdf (Postprint), 684KB
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Schreyer, Kaib, Wakchaure, Obradors, Properzi, Lee, List 2018.pdf
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 Creators:
Schreyer, Lucas1, Author              
Kaib, Philip S. J.1, Author              
Wakchaure, Vijay N.1, Author              
Obradors, Carla1, Author              
Properzi, Roberta1, Author              
Lee, Sunggi1, Author              
List, Benjamin1, Author              
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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 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.

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Language(s): eng - English
 Dates: 2018-08-072018-10-122018-10-12
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1126/science.aau0817
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Title: Science
  Abbreviation : Science
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Association for the Advancement of Science
Pages: - Volume / Issue: 362 (6411) Sequence Number: - Start / End Page: 216 - 219 Identifier: ISSN: 0036-8075
CoNE: https://pure.mpg.de/cone/journals/resource/991042748276600_1