Journal
ACS CATALYSIS
Volume 7, Issue 6, Pages 3929-3933Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00794
Keywords
organocatalysis; N-heterocyclic carbene; coupling; chiral diesters; bromo-lactide
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Funding
- US National Science Foundation [NSF-1507702]
- W.M. Keck Foundation
- King Abdullah University of Science and Technology (KAUST)
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In the presence of a N-heterocyclic carbene (NHC) in THF, Br-substituted L-lactide (Br-LA) unexpectedly undergoes exclusive coupling with THF to form a chiral omega-bromo-alpha-keto-diester. This coupling reaction is completely selective (in a precise 1:1 fashion), readily scalable (>20 g scale), and extremely efficient (with only 50 ppm of NHC loading). Other cyclic ethers and carbonates can also undergo similar coupling with Br-LA, thus offering a class of Br-functionalized chiral diesters with various functions and chain lengths. Combined experimental and computational studies led to a coupling mechanism that proceeds through an anion (bromide)-mediated catalytic cycle, rather than an apparent NHC-catalyzed cycle.
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