Stereoselective organozinc addition reactions to 1,2-dihydropyrans for the assembly of complex pyran structures

Organic Letters

Volumn 4, Issue 2, 2002, Pages 293-295

  Steinhuebel, Dietrich P ^a   Fleming, James J ^a   Du Bois, J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; PYRAN DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; ORGANOMETALLIC COMPOUNDS; PYRANS; STEREOISOMERISM; ZINC;

EID: 0037165407     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010273e     Document Type: Article

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29. Dihydropyran starting materials were prepared following published protocols; see: (a) Rainier, J. D.; Alhvein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386. (b) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413-9436. (c) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089.
30. N2′-type addition.
31. 1H NMR of the unpurified reaction mixture.
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36. Examples of such natural products include: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027-11028. (b) Nicolaou, K. C; Patron, A. P.; Ajito, K.; Richter, P. K.; Khatuya, H.; Bertinato, P.; Miller, R. A.; Tomaszewski, M. J. Chem. Eur. J. 1996, 2, 847-868. (c) Paterson, I.; Smith, J. D. Tetrahedron Lett. 1993, 34, 5351-5354.
37. Examples of such natural products include: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027-11028. (b) Nicolaou, K. C; Patron, A. P.; Ajito, K.; Richter, P. K.; Khatuya, H.; Bertinato, P.; Miller, R. A.; Tomaszewski, M. J. Chem. Eur. J. 1996, 2, 847-868. (c) Paterson, I.; Smith, J. D. Tetrahedron Lett. 1993, 34, 5351-5354.
38. 1H NMR coupling constant and NOE data.
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