Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions.
As the first N-centered heteroaromatic nucleophile for organocatalytic cascade reactions, pyrroles underwent the enantio- and diastereoselective organocatalytic cascade conjugate addition-aldol reactions of α,β-unsaturated aldehydes that afford the highly functionalized chiral pyrrolizines bearing three consecutive stereocenters in good yields, high enantioselectivities (90-98% ee), and excellent diastereoselectivities (>20:1 dr in all cases).
Bae
Ju-Yeon
JY
Department of Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea.
Lee
Hyo-Jun
HJ
Youn
Seok-Ho
SH
Kwon
Su-Hyun
SH
Cho
Chang-Woo
CW
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D011758:Pyrroles; C116609:3-hydroxybutanal