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- Title
Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes.
- Authors
Kaib, Philip S. J.; Schreyer, Lucas; Lee, Sunggi; Properzi, Roberta; List, Benjamin
- 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 reaction, has remained elusive. 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.
- Subjects
CHEMICAL alcohol synthesis; METHYLSILANE; ALLYLATION; ALDEHYDES; ORGANOCATALYSIS; ENANTIOSELECTIVE catalysis; CARBON-carbon bonds
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 42, p13394
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201607828