Chiral tartrate-derived dioxaborolidine: A simple and practical catalyst for enantioselective Diels-Alder reaction

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2989-2992

  Loh, Teck Peng ^a   Wang, Rui Bin ^a   Sim, Keng Yeow ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

BETULACEAE;

EID: 0029922345     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00481-9     Document Type: Article

References (31)

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29. (b) Johnson, J.R.; Van Campen, Jr, M.G.; Grummitt, O. J. Am. Chem. Soc. 1938, 60, 111-115. The catalyst complex was made in the following method: To a 25 mL round-bottom flask equipped with a magnetic stirring bar was added L-diisopropyl tartrate ester (0.054 mL, 0.28 mmol) and benzyl boronic acid (45.7 mg, 0.336 mmol) under nitrogen. The flask was charged with toluene (16 mL) and then fitted with an extractive drying apparatus and a reflux condenser. The reaction mixture was then heated to reflux for 18 h. The resulting catalyst solution was used directly for the Diels-Alder reaction.
30. Loh, T.-P. Part I: Design of Catalysts for Enantioselective Diels-Alder Reaction; Part II: Stereocontrolled Total Synthesis of (+)-and (-)-Epibatidine and Analogs, Harvard University, 1994.
31. This research was assisted financially by the National University of Singapore (RP930657, RP940633, RP950609). We are also grateful to Singapore Government for providing a research scholarship to RBW.