Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst

Organic Letters

Volumn 1, Issue 1, 1999, Pages 157-160

  Corey, E J ^a   Grogan, Michael J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZHYDRYL DERIVATIVE; BICYCLO COMPOUND; GUANIDINE DERIVATIVE; HYDROGEN CYANIDE; IMINE; NITRILE; SCHIFF BASE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BENZHYDRYL COMPOUNDS; BICYCLO COMPOUNDS; CATALYSIS; GUANIDINES; HYDROGEN CYANIDE; IMINES; MODELS, MOLECULAR; NITRILES; SCHIFF BASES; STEREOISOMERISM;

EID: 0033564990     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990623l     Document Type: Article

References (13)

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7. N-Benzhydrylimines were prepared by combining the aldehyde and N-benzhydrylamine (5 mmol each) in benzene (5 mL) at 23°C, removing solvent in vacuo, filtering a benzene solution of the residue through activated silica gel (0.2 g), and concentrating to the pure imines.
8. +].
9. 4, and concentrated to give amino nitrile 3 that could be further purified by silica gel chromatography (1% ethyl acetate-hexanes). Basification with 1 N NaOH of the oxalic acid wash and extraction with ethyl acetate and concentration allows recovery of 1 (80-90% yield). Enantioselectivity was analyzed by chiral HPLC with Chiralpak AD, Chiralpak AS or Chiralcel OJ columns with 2-propanol -hexanes as eluent.
10. Corey, E. J.; Ohtani, M. Tetrahedron. Lett. 1989, 30, 5227.
11. 2; orthorhombic; P2(1)2(1)2(1); a = 8.7909(3) Å; b = 10.4417(4) Å; c = 22.3969(3) Å; α = β = γ = 90°; Z = 6; T = 213 K; R1[I > 2σ(I)] = 0.0416.
12. See for example: (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038.
13. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.