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Volumn 74, Issue 1, 2009, Pages 64-74

Stereopentads derived from a sequence of Mukaiyama aldolization and free radical reduction on α-methyl-β-alkoxy aldehydes: A general strategy for efficient polypropionate synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ALDOLIZATION; CHEMICAL EQUATIONS; DIASTEREOMERIC; HYDROGEN TRANSFERS; KEY INTERMEDIATES; RADICAL REDUCTIONS; SYNTHESIS OF;

EID: 58149289855     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8021583     Document Type: Article
Times cited : (28)

References (92)
  • 24
    • 21844468996 scopus 로고    scopus 로고
    • This group has also studied the use of oxymercuration for propionate synthesis. See: (c) Defosseux, M, Blanchard, N, Meyer, C, Cossy, J. Tetrahedron 2005, 61, 7632, and references therein
    • This group has also studied the use of oxymercuration for propionate synthesis. See: (c) Defosseux, M.; Blanchard, N.; Meyer, C.; Cossy, J. Tetrahedron 2005, 61, 7632, and references therein.
  • 25
    • 58149286678 scopus 로고    scopus 로고
    • Other very interesting approaches for propionate and polypropionate synthesis have also been developed over the years. See: (a) Kishi, Y. Tetrahedron 1981, 23, 3873
    • Other very interesting approaches for propionate and polypropionate synthesis have also been developed over the years. See: (a) Kishi, Y. Tetrahedron 1981, 23, 3873.
  • 47
    • 0013372519 scopus 로고    scopus 로고
    • Masamune and Hoffmann work with the complex enol borane and crotylboronate: (a) Short, R. P.; Masamune, S. Tetrahedron Lett. 1987, 28, 2841.
    • Masamune and Hoffmann work with the complex enol borane and crotylboronate: (a) Short, R. P.; Masamune, S. Tetrahedron Lett. 1987, 28, 2841.
  • 55
    • 58149311593 scopus 로고    scopus 로고
    • The others were constructed by switching the terminal hydroxy group of isomers previously obtained. See ref 4
    • The others were constructed by switching the terminal hydroxy group of isomers previously obtained. See ref 4.
  • 67
    • 15844376790 scopus 로고    scopus 로고
    • Evans reported a very interesting investigation about the stereochemical consequences of α-alkyl-β-alkoxy aldehyde in Mukaiyama aldolization. See: (a) Evans, D. A, Dart, M. J, Duffy, J. L, Yang, M. J. J. Am. Chem. Soc. 1996, 118, 4322
    • Evans reported a very interesting investigation about the stereochemical consequences of α-alkyl-β-alkoxy aldehyde in Mukaiyama aldolization. See: (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. J. J. Am. Chem. Soc. 1996, 118, 4322.
  • 69
    • 58149316740 scopus 로고    scopus 로고
    • 1H NMR analysis and were used directly in the Mukaiyama reactions without chromatographic purification to avoid racemization. For all detailed procedures, see Supporting Information.
    • 1H NMR analysis and were used directly in the Mukaiyama reactions without chromatographic purification to avoid racemization. For all detailed procedures, see Supporting Information.
  • 71
    • 0001370202 scopus 로고    scopus 로고
    • This intermediate is not necessarily the reactive specie since the Curtin-Hammett principle can be evoked. However, many stereoselective nucleophilic additions with TiCl4 and SnCl4 have been explained by models supported by NMR spectroscopy. See: Keck, G. E, Andrus, M. B, Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136, and references therein
    • 4 have been explained by models supported by NMR spectroscopy. See: Keck, G. E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136, and references therein.
  • 73
    • 0001486864 scopus 로고    scopus 로고
    • 2AlCl in Diels-Alder reactions. See: Castellino, S.; Wesley, J. D. J. Am. Chem. Soc. 1993, 115, 2986.
    • 2AlCl in Diels-Alder reactions. See: Castellino, S.; Wesley, J. D. J. Am. Chem. Soc. 1993, 115, 2986.
  • 75
    • 58149314675 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 90
    • 58149279944 scopus 로고    scopus 로고
    • See the Supporting Information for general methods and procedures
    • See the Supporting Information for general methods and procedures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.