TY - JOUR
T1 - Organocatalytic Enantioselective [1,2]-Stevens Rearrangement of Azetidinium Salts
AU - De Oliveira Silva, Ana
AU - Masand, Shruti A.
AU - Farah, Abdikani Omar
AU - Laddusaw, Jacqueline
AU - Urbina, Kelvin
AU - Rodríguez-Alvarado, Melanie
AU - Lalancette, Roger A.
AU - Cheong, Paul Ha Yeon
AU - Brenner-Moyer, Stacey E.
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024/6/21
Y1 - 2024/6/21
N2 - The first organocatalyzed enantioselective [1,2]-Stevens rearrangement is reported. 4-Alkylideneproline derivatives are produced in up to 86% yield and in up to 90:10 er, with recrystallization enhancing er up to >99.5:0.5. Product configuration was opposite that predicted by existing stereochemical models for this organocatalyst class, and DFT calculations revealed a novel mode of asymmetric induction. The adaptability of this catalytic strategy for asymmetric [1,2]-Stevens rearrangements of other heterocyclic amines was demonstrated.
AB - The first organocatalyzed enantioselective [1,2]-Stevens rearrangement is reported. 4-Alkylideneproline derivatives are produced in up to 86% yield and in up to 90:10 er, with recrystallization enhancing er up to >99.5:0.5. Product configuration was opposite that predicted by existing stereochemical models for this organocatalyst class, and DFT calculations revealed a novel mode of asymmetric induction. The adaptability of this catalytic strategy for asymmetric [1,2]-Stevens rearrangements of other heterocyclic amines was demonstrated.
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U2 - 10.1021/acs.joc.4c00534
DO - 10.1021/acs.joc.4c00534
M3 - Article
AN - SCOPUS:85195592866
SN - 0022-3263
VL - 89
SP - 9063
EP - 9067
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 12
ER -