The intramolecular salt effect in chiral auxiliaries. Enhanced diastereoselectivity in a nitrile oxide cycloaddition via rational transition state stabilization

Tetrahedron Letters

Volumn 40, Issue 7, 1999, Pages 1285-1288

  Raposo, César ^a   Wilcox, Craig S ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CHLOROFORM; DICHLOROMETHANE; NITRILE; OXIDE; REAGENT; SOLVENT; TOLUENE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033547981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02692-6     Document Type: Article

References (14)

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3. b) Warshel, A.; Naray-Szabo, G.; Sussman, F.; Hwang, J-K. Biochemistry, 1989, 28, 3629-3637. Fersht, A. Enzyme Structure and Mechanism, Freeman: New York, 1985.
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13. Benzonitrile oxide was generated following the procedure of reference 4, starting from the corresponding N-chloro oxime by treatment with triethylamine unless indicated in the text. The triethylammonium chloride was removed by filtration whenever possible.
14. Brzeznski, B.; Grech, E.; Malarki, Z.; Sobczyk, L. J. Chem. Soc. Perkin Trans.2 1991, 857.