Beta-isocupreidine-catalyzed Baylis-Hillman reaction of chiral N-boc-alpha-amino aldehydes.
[Structure: see text] Beta-isocupreidine (beta-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-alpha-amino aldehydes and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, L-substrates show excellent syn selectivity and high reactivity in contrast to D-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity.
Nakano
Ayako
A
Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki-852-8521, Japan.
Takahashi
Keisuke
K
Ishihara
Jun
J
Hatakeyama
Susumi
S
D000447:Aldehydes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006912:Hydroxyquinolines / Q000737:chemistry*; D015394:Molecular Structure; D011812:Quinuclidines / Q000737:chemistry*
D000447:Aldehydes; D006571:Heterocyclic Compounds; D006912:Hydroxyquinolines; D011812:Quinuclidines; C517075:beta-isocupreidine