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Bendelsmith, Andrew J; Kim, Seohyun Chris; Wasa, Masayuki; Roche, Stéphane P; Jacobsen, Eric N
Journal of the American Chemical Society, 07/2019, Letnik: 141, Številka: 29Journal Article
We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to -carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted S 2 mechanism.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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