On the role of chiral catalysts in the alkenyl zirconocene/zinc addition to aldehydes: A study of ligand loading and asymmetric amplification

Chirality

Volumn 15, Issue 3, 2003, Pages 208-212

  Wipf, Peter ^a   Jayasuriya, Nilukshi ^a   Ribe, Seth ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Aminoalcohol; Aminophenol; Aminothiophenol; Catalysis; Chiral allylic alcohols; Chiral induction; Dimethylzinc; Ligand aggregation; Nonlinear effects; Transmetalation

Indexed keywords

ALKENE; ALLYL ALCOHOL; AMINOALCOHOL; AMINOPHENOL; LIGAND; THIOPHENOL DERIVATIVE; ZINC; ZINC DERIVATIVE; ZIRCONOCENE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0037284753     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10176     Document Type: Article

References (34)

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15. For related zirconium-zinc transmetalations, see: (a) Wipf P, Kendall C. Novel applications of alkenyl zirconocenes. Chem Eur J 2002;8: 1778-1784. (b) Wipf P, Kendall C. Tandem zirconocene homologation - aldimine addition. Org Lett 2001;3:2773-2776. (c) Wipf P, Kendall C, Stephenson CRJ. Three-component aldimine addition - cyclopropanation. An efficient new methodology for amino cyclopropane synthesis. J Am Chem Soc 2001;123:5122-5123. (d) Wipf P, Coish PDG. Total synthesis of (±)-nisamycin. J Org Chem 1999;64: 5053-5061. (e) Wipf P, Coish PDG. Organozirconocene-mediated polyene synthesis: preparation of asukamycin and manumycin A side chains. Tetrahedron Lett 1997;38:5073-5076. (f) Wipf P, Xu W, Takahashi H, Jahn H, Coish PDG. Synthetic applications of organozirconocenes. Pure Appl Chem 1997;69:639-644, and references therein. (g) Shen R, Lin CT, Porco JA. Total synthesis and stereochemical assignment of the salicylate antitumor antibiotic lobatamide C. J Am Chem Soc 2002;124:5650-5651. (h) Wipf P, Reeves JT. A formal total synthesis of leucascandrolide A. Chem Commun 2002:2066-2067.
16. For related zirconium-zinc transmetalations, see: (a) Wipf P, Kendall C. Novel applications of alkenyl zirconocenes. Chem Eur J 2002;8: 1778-1784. (b) Wipf P, Kendall C. Tandem zirconocene homologation - aldimine addition. Org Lett 2001;3:2773-2776. (c) Wipf P, Kendall C, Stephenson CRJ. Three-component aldimine addition - cyclopropanation. An efficient new methodology for amino cyclopropane synthesis. J Am Chem Soc 2001;123:5122-5123. (d) Wipf P, Coish PDG. Total synthesis of (±)-nisamycin. J Org Chem 1999;64: 5053-5061. (e) Wipf P, Coish PDG. Organozirconocene-mediated polyene synthesis: preparation of asukamycin and manumycin A side chains. Tetrahedron Lett 1997;38:5073-5076. (f) Wipf P, Xu W, Takahashi H, Jahn H, Coish PDG. Synthetic applications of organozirconocenes. Pure Appl Chem 1997;69:639-644, and references therein. (g) Shen R, Lin CT, Porco JA. Total synthesis and stereochemical assignment of the salicylate antitumor antibiotic lobatamide C. J Am Chem Soc 2002;124:5650-5651. (h) Wipf P, Reeves JT. A formal total synthesis of leucascandrolide A. Chem Commun 2002:2066-2067.
17. For related zirconium-zinc transmetalations, see: (a) Wipf P, Kendall C. Novel applications of alkenyl zirconocenes. Chem Eur J 2002;8: 1778-1784. (b) Wipf P, Kendall C. Tandem zirconocene homologation - aldimine addition. Org Lett 2001;3:2773-2776. (c) Wipf P, Kendall C, Stephenson CRJ. Three-component aldimine addition - cyclopropanation. An efficient new methodology for amino cyclopropane synthesis. J Am Chem Soc 2001;123:5122-5123. (d) Wipf P, Coish PDG. Total synthesis of (±)-nisamycin. J Org Chem 1999;64: 5053-5061. (e) Wipf P, Coish PDG. Organozirconocene-mediated polyene synthesis: preparation of asukamycin and manumycin A side chains. Tetrahedron Lett 1997;38:5073-5076. (f) Wipf P, Xu W, Takahashi H, Jahn H, Coish PDG. Synthetic applications of organozirconocenes. Pure Appl Chem 1997;69:639-644, and references therein. (g) Shen R, Lin CT, Porco JA. Total synthesis and stereochemical assignment of the salicylate antitumor antibiotic lobatamide C. J Am Chem Soc 2002;124:5650-5651. (h) Wipf P, Reeves JT. A formal total synthesis of leucascandrolide A. Chem Commun 2002:2066-2067.
18. For related zirconium-zinc transmetalations, see: (a) Wipf P, Kendall C. Novel applications of alkenyl zirconocenes. Chem Eur J 2002;8: 1778-1784. (b) Wipf P, Kendall C. Tandem zirconocene homologation - aldimine addition. Org Lett 2001;3:2773-2776. (c) Wipf P, Kendall C, Stephenson CRJ. Three-component aldimine addition - cyclopropanation. An efficient new methodology for amino cyclopropane synthesis. J Am Chem Soc 2001;123:5122-5123. (d) Wipf P, Coish PDG. Total synthesis of (±)-nisamycin. J Org Chem 1999;64: 5053-5061. (e) Wipf P, Coish PDG. Organozirconocene-mediated polyene synthesis: preparation of asukamycin and manumycin A side chains. Tetrahedron Lett 1997;38:5073-5076. (f) Wipf P, Xu W, Takahashi H, Jahn H, Coish PDG. Synthetic applications of organozirconocenes. Pure Appl Chem 1997;69:639-644, and references therein. (g) Shen R, Lin CT, Porco JA. Total synthesis and stereochemical assignment of the salicylate antitumor antibiotic lobatamide C. J Am Chem Soc 2002;124:5650-5651. (h) Wipf P, Reeves JT. A formal total synthesis of leucascandrolide A. Chem Commun 2002:2066-2067.
19. For related zirconium-zinc transmetalations, see: (a) Wipf P, Kendall C. Novel applications of alkenyl zirconocenes. Chem Eur J 2002;8: 1778-1784. (b) Wipf P, Kendall C. Tandem zirconocene homologation - aldimine addition. Org Lett 2001;3:2773-2776. (c) Wipf P, Kendall C, Stephenson CRJ. Three-component aldimine addition - cyclopropanation. An efficient new methodology for amino cyclopropane synthesis. J Am Chem Soc 2001;123:5122-5123. (d) Wipf P, Coish PDG. Total synthesis of (±)-nisamycin. J Org Chem 1999;64: 5053-5061. (e) Wipf P, Coish PDG. Organozirconocene-mediated polyene synthesis: preparation of asukamycin and manumycin A side chains. Tetrahedron Lett 1997;38:5073-5076. (f) Wipf P, Xu W, Takahashi H, Jahn H, Coish PDG. Synthetic applications of organozirconocenes. Pure Appl Chem 1997;69:639-644, and references therein. (g) Shen R, Lin CT, Porco JA. Total synthesis and stereochemical assignment of the salicylate antitumor antibiotic lobatamide C. J Am Chem Soc 2002;124:5650-5651. (h) Wipf P, Reeves JT. A formal total synthesis of leucascandrolide A. Chem Commun 2002:2066-2067.
20. For related zirconium-zinc transmetalations, see: (a) Wipf P, Kendall C. Novel applications of alkenyl zirconocenes. Chem Eur J 2002;8: 1778-1784. (b) Wipf P, Kendall C. Tandem zirconocene homologation - aldimine addition. Org Lett 2001;3:2773-2776. (c) Wipf P, Kendall C, Stephenson CRJ. Three-component aldimine addition - cyclopropanation. An efficient new methodology for amino cyclopropane synthesis. J Am Chem Soc 2001;123:5122-5123. (d) Wipf P, Coish PDG. Total synthesis of (±)-nisamycin. J Org Chem 1999;64: 5053-5061. (e) Wipf P, Coish PDG. Organozirconocene-mediated polyene synthesis: preparation of asukamycin and manumycin A side chains. Tetrahedron Lett 1997;38:5073-5076. (f) Wipf P, Xu W, Takahashi H, Jahn H, Coish PDG. Synthetic applications of organozirconocenes. Pure Appl Chem 1997;69:639-644, and references therein. (g) Shen R, Lin CT, Porco JA. Total synthesis and stereochemical assignment of the salicylate antitumor antibiotic lobatamide C. J Am Chem Soc 2002;124:5650-5651. (h) Wipf P, Reeves JT. A formal total synthesis of leucascandrolide A. Chem Commun 2002:2066-2067.
21. For related zirconium-zinc transmetalations, see: (a) Wipf P, Kendall C. Novel applications of alkenyl zirconocenes. Chem Eur J 2002;8: 1778-1784. (b) Wipf P, Kendall C. Tandem zirconocene homologation - aldimine addition. Org Lett 2001;3:2773-2776. (c) Wipf P, Kendall C, Stephenson CRJ. Three-component aldimine addition - cyclopropanation. An efficient new methodology for amino cyclopropane synthesis. J Am Chem Soc 2001;123:5122-5123. (d) Wipf P, Coish PDG. Total synthesis of (±)-nisamycin. J Org Chem 1999;64: 5053-5061. (e) Wipf P, Coish PDG. Organozirconocene-mediated polyene synthesis: preparation of asukamycin and manumycin A side chains. Tetrahedron Lett 1997;38:5073-5076. (f) Wipf P, Xu W, Takahashi H, Jahn H, Coish PDG. Synthetic applications of organozirconocenes. Pure Appl Chem 1997;69:639-644, and references therein. (g) Shen R, Lin CT, Porco JA. Total synthesis and stereochemical assignment of the salicylate antitumor antibiotic lobatamide C. J Am Chem Soc 2002;124:5650-5651. (h) Wipf P, Reeves JT. A formal total synthesis of leucascandrolide A. Chem Commun 2002:2066-2067.
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