Aldol Synthesis with an Aqueous Solution of Formalin

Synlett

Volumn , Issue 14, 2003, Pages 2219-2221

  Ozasa, Nobuko ^a   Wadamoto, Manabu ^b   Ishihara, Kazuaki ^a   Yamamoto, Hisashi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Aldol reaction; BINAP AgOTf catalyst; Enantioselective; Formalin aqueous solution; Silyl enol ether

Indexed keywords

AMMONIUM DERIVATIVE; BASE; ETHER DERIVATIVE; FLUORIDE; FORMALDEHYDE; LEWIS ACID; TRIMETHYLSILYL DERIVATIVE;

ALDOL REACTION; AQUEOUS SOLUTION; ARTICLE; ENANTIOSELECTIVITY; METHYLATION;

EID: 0242408207     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42089     Document Type: Article

References (24)

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12. (b) See also: Noyori, R.; Nishida, I.; Sakata, J. Tetrahedron Lett. 1980, 21, 2085.
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20. To our knowledge, there is now only one report of cat. enantioselective hydroxymethylation using formaline aq solution, and this is the first report in which chiral Lewis acid is utilized for activation: (a) Fujii, M.; Sato, Y.; Aida, S. Chem. Exp. 1992, 7, 309. (b) Catalytic enantioselective ene reaction using formaldehyde is also reported: Mikami, K.; Yoshida, A. Synlett 1995, 29.
21. To our knowledge, there is now only one report of cat. enantioselective hydroxymethylation using formaline aq solution, and this is the first report in which chiral Lewis acid is utilized for activation: (a) Fujii, M.; Sato, Y.; Aida, S. Chem. Exp. 1992, 7, 309. (b) Catalytic enantioselective ene reaction using formaldehyde is also reported: Mikami, K.; Yoshida, A. Synlett 1995, 29.
22. Baliri, P. L.; Catelani, G.; Giori, R.; Mastrorilli, E. Enantiomer 1998, 3, 357.
23. Schoofs, A.; Guette, J. P.; Horeau, A. Bull. Soc. Chim. Fr. 1976, 7-8, 1215.
24. The reaction mixture is barely stirrable without being unfrozen.