Abstract
Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of α-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although α-(p -methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, α-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.
| Original language | English |
|---|---|
| Pages (from-to) | 1835-1839 |
| Number of pages | 5 |
| Journal | Synlett |
| Volume | 30 |
| Issue number | 15 |
| DOIs | |
| Publication status | Published - Jan 1 2019 |
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Keywords
- 1,3-dipolar cycloaddition
- acyloxyacroleins
- asymmetric catalysis
- isoxazolidines
- nitrones
- organocatalysis
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts. / Kidou, Chihiro; Mizoguchi, Haruki; Nehira, Tatsuo; Sakakura, Akira.
In: Synlett, Vol. 30, No. 15, 01.01.2019, p. 1835-1839.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts
AU - Kidou, Chihiro
AU - Mizoguchi, Haruki
AU - Nehira, Tatsuo
AU - Sakakura, Akira
PY - 2019/1/1
Y1 - 2019/1/1
N2 - Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of α-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although α-(p -methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, α-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.
AB - Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of α-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although α-(p -methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, α-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.
KW - 1,3-dipolar cycloaddition
KW - acyloxyacroleins
KW - asymmetric catalysis
KW - isoxazolidines
KW - nitrones
KW - organocatalysis
UR - http://www.scopus.com/inward/record.url?scp=85071764873&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85071764873&partnerID=8YFLogxK
U2 - 10.1055/s-0039-1690133
DO - 10.1055/s-0039-1690133
M3 - Article
VL - 30
SP - 1835
EP - 1839
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 15
ER -