Cr(III)(salen)Cl catalyzed enantioselective intramolecular addition of tertiary enamides to ketones: a general access to enantioenriched 1H-pyrrol-2(3H)-one derivatives bearing a hydroxylated quaternary carbon atom.
Catalyzed by a chiral Cr(III)(salen)Cl complex 3e, tertiary enamides 1 underwent an efficient and enantioselective intramolecular addition reaction to an activated carbonyl moiety to produce in excellent yield highly enantioenriched 1H-pyrrol-2(3H)-one derivatives 2 that bear a hydroxylated quaternary carbon atom. The synthetic application of resulting compounds has been demonstrated in the synthesis of (3S,5S)-3,5-diphenyl-3-pyrrolidinol.
Yang
Luo
L
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Wang
De-Xian
DX
Huang
Zhi-Tang
ZT
Wang
Mei-Xiang
MX
D000577:Amides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000577:Amides; D007659:Ketones; D009942:Organometallic Compounds; D011758:Pyrroles; D002244:Carbon