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Volumn 61, Issue 11, 1996, Pages 3588-3589

Diastereoselective cyclizations of 1,3-dioxan-2-yl radicals: Chiral acyl radical equivalents

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EID: 0001281736     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960705c     Document Type: Article
Times cited : (17)

References (39)
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    • Lead references: (a) Crich, D.; Sun, S.; Brunckova J. Org. Chem. 1996, 61, 605. (b) Yamazaki, N.; Eichenberger, E. Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (c) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (d) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
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    • trans-4,6-Disubstituted 2,2-dimethyl-1,3-dioxanes adopt twist-boat conformations: (a) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (b) Rychnovsky, S. D.; Yang, G.; Powers, J. P. J. Org. Chem. 1993, 58, 5251.
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    • trans-4,6-Disubstituted 2,2-dimethyl-1,3-dioxanes adopt twist-boat conformations: (a) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (b) Rychnovsky, S. D.; Yang, G.; Powers, J. P. J. Org. Chem. 1993, 58, 5251.
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    • Aldrich Chemical Co., Milwaukee, WI
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    • For the stereochemistry of quenching of simple 9-decalinyl radicals with tin hydrides see: Greene, F. D.; Lowry, N. N. J. Org. Chem. 1967, 32, 882.
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    • note
    • The two alkyl groups R′ and R″ (5) in 10 and 27 severely restrict the number of boat and twist boat conformers resulting in formation of only one isomer (14 and 33) from exo-face quenching as opposed to the mixture (22) obtained when R′ = H as in 11.
  • 30
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    • note
    • The basic structural motif could be obtained from selected terpenoids such as hederagenin and aphidicolin, but their relative inaccessibility renders them unattractive for use as chiral auxiliaries.
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    • note
    • Chiral lanthanide shift reagents were unsatisfactory.
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    • Although the Pirkle solvating agent is usually applied to more polar species, NMR resolution of simple lactones has been reported: (a) Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384. (b) Pirkle, W. H.; Adams, P. E. J. Org. Chem. 1978, 43, 378.
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    • Although the Pirkle solvating agent is usually applied to more polar species, NMR resolution of simple lactones has been reported: (a) Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384. (b) Pirkle, W. H.; Adams, P. E. J. Org. Chem. 1978, 43, 378.
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    • note
    • 2 in acetone was found to minimize this problem.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.