Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes

Organic Letters

Volumn 9, Issue 1, 2007, Pages 97-100

  Suga, Hiroyuki ^a   Funyu, Akira ^a   Kakehi, Akikazu ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACRYLOYL 2 OXAZOLIDINONE; 3-ACRYLOYL-2-OXAZOLIDINONE; AZO COMPOUND; AZOMETHINE; BINAPHTHYLDIIMINE NI(II); DRUG DERIVATIVE; IMINE; LIGAND; NICKEL; ORGANOMETALLIC COMPOUND; OXAZOLONE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

AZO COMPOUNDS; CATALYSIS; IMINES; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; OXAZOLONE; STEREOISOMERISM; THIOSEMICARBAZONES;

EID: 33846436800     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062675y     Document Type: Article

References (36)

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30. 3 for 24 h, 49:51, 52%.
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34. It is noteworthy that a 5,5-dimethyl moiety played an important role for high enantioselectivity. The reaction of 1-benzylidene-3-oxopyrazolidin-1-ium-2- ide under conditions similar to entry 4 gave a trans-adduct selectively (trans/cis = 93:7) with only 35% ee (yield of 86%).
35. 1H NMR study indicated that the Ni(II) complex mainly coordinated to 1a rather than to 2.
36. The structure of the complex was optimized by PM3 calculations (Spartan 04).