Neutral coordinate-organocatalysts in organic synthesis: Allylation of acylhydrazones with allyltrichlorosilanes

Advanced Synthesis and Catalysis

Volumn 346, Issue 9-10, 2004, Pages 1023-1034

  Kobayashi, Shu ^a,b   Sugiura, Masaharu ^a,c,d,e   Ogawa, Chikako ^a,f,g  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^d FLORIDA STATE UNIVERSITY   (United States)

^e JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^f SWISS FEDERAL INSTITUTE OF TECHNOLOGY   (Switzerland)

^g JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

Author keywords

Allylation; Amides; C C bond formation; Hydrazones; Organic catalysis; Phosphane oxides; Sulfoxides

Indexed keywords

AMINE; HYDRAZONE DERIVATIVE; IMINE; SILANE DERIVATIVE;

ALLYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; RACEMIZATION; REVIEW; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 5144223357     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404101     Document Type: Review

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47. Based on this definition, several amines which activate nucleophiles in addition to carbonyl and related compounds are classified into NCOs. In these cases, while the molecules are uncharged and neutral, reaction mixtures would be somehow basic. Other terms, "external (chiral) ligand control" or "(chiral) coordinating agents," have been used for the same category of the catalysis, see: a) K. Tomioka, Synthesis 1990, 541; b) K. Tomioka, M. Hasegawa, J. Synth. Org. Chem. Jpn. 2000, 58, 24; c) H. Doi, T. Sakai, M. Iguchi, K. Yamada, K. Tomioka, J. Am. Chem. Soc. 2003, 125, 2886, and references cited therein; d) K. Tomooka, J. Synth. Org. Chem. Jpn. 2001, 59, 322; e) K. Tomooka, K. Yamamoto, T. Nakai, Angew. Chem. Int. Ed. 1999, 38, 3741, and references cited therein.
48. Based on this definition, several amines which activate nucleophiles in addition to carbonyl and related compounds are classified into NCOs. In these cases, while the molecules are uncharged and neutral, reaction mixtures would be somehow basic. Other terms, "external (chiral) ligand control" or "(chiral) coordinating agents," have been used for the same category of the catalysis, see: a) K. Tomioka, Synthesis 1990, 541; b) K. Tomioka, M. Hasegawa, J. Synth. Org. Chem. Jpn. 2000, 58, 24; c) H. Doi, T. Sakai, M. Iguchi, K. Yamada, K. Tomioka, J. Am. Chem. Soc. 2003, 125, 2886, and references cited therein; d) K. Tomooka, J. Synth. Org. Chem. Jpn. 2001, 59, 322; e) K. Tomooka, K. Yamamoto, T. Nakai, Angew. Chem. Int. Ed. 1999, 38, 3741, and references cited therein.
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50. Based on this definition, several amines which activate nucleophiles in addition to carbonyl and related compounds are classified into NCOs. In these cases, while the molecules are uncharged and neutral, reaction mixtures would be somehow basic. Other terms, "external (chiral) ligand control" or "(chiral) coordinating agents," have been used for the same category of the catalysis, see: a) K. Tomioka, Synthesis 1990, 541; b) K. Tomioka, M. Hasegawa, J. Synth. Org. Chem. Jpn. 2000, 58, 24; c) H. Doi, T. Sakai, M. Iguchi, K. Yamada, K. Tomioka, J. Am. Chem. Soc. 2003, 125, 2886, and references cited therein; d) K. Tomooka, J. Synth. Org. Chem. Jpn. 2001, 59, 322; e) K. Tomooka, K. Yamamoto, T. Nakai, Angew. Chem. Int. Ed. 1999, 38, 3741, and references cited therein.
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