Generation of 2-substituted-2-metallo-1,3-dithianes and their coupling with 1,2-disubstituted epoxides at room temperature

Synlett

Volumn , Issue 8, 1998, Pages 936-938

  Ide, Mitsuaki ^a   Yasuda, Minora ^a   Nakata, Masaya ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 0002708787     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1825     Document Type: Article

References (55)

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20. 2, -30 °C, 0.5 h, then CSA, MeOH, rt, 1 h; (5) to 6: TBDPSCl, imidazole, DMF, rt, 0.5 h, 58% for five steps. to 9: TBSCl, imidazole, DMF, 0 °C, 0.5 h, 55% for five steps. The enantiomer of 6 was prepared by Smith et al., see ref 3h.
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22. 2, rt, 3 h, 74%).
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36. Besides them, the compound i was produced as a by-product derived from epoxide 7 in less than 5% yield. (Chemical Equation Presented) Figure 1
37. 2, 0 °C, 0.5 h, then CSA, MeOH, rt, 1 h; (4) TBDPSCl, imidazole, DMF, rt, 3 h, 49% for four steps.
38. 2, rt, 1 h, 88%), 1,3-dithiane addition (1,3-dithiane, n-BuLi, THF, -30 °C, 1 h) and silylation (TBDPSCl, DMAP, DMF, 100 °C, 36 h, 89% for two steps).
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