Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.
An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Hui
H
Lv
Bhoopendra
B
Tiwari
Junming
J
Mo
Chong
C
Xing
Yonggui Robin
YR
Chi
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D007097:Imines; D007211:Indoles; D007769:Lactams; D009570:Nitriles; D000078183:Oxindoles; D013141:Spiro Compounds; C542835:ketimine; C022960:2-oxindole; C030011:carbene; D007510:Isatin; D008697:Methane