2018
DOI: 10.3987/com-18-13940
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Lewis Acid Promoted Prins Cyclization Using Non-Conjugated Diene Alcohol: Sequential Reactions Terminated by Fluoride Ion

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Cited by 6 publications
(6 citation statements)
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“…4)). The same process is described in a previous report [23]. As for the final step of halogenation of E, such as chlorination, there is the possibility that Cl − derived from TMSCl, AlCl3, [HOAlCl3] − , and/or CH2Cl2 solvent would react with E to form 3.…”
Section: Resultsmentioning
confidence: 89%
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“…4)). The same process is described in a previous report [23]. As for the final step of halogenation of E, such as chlorination, there is the possibility that Cl − derived from TMSCl, AlCl3, [HOAlCl3] − , and/or CH2Cl2 solvent would react with E to form 3.…”
Section: Resultsmentioning
confidence: 89%
“…Table 1 shows the results of the reaction optimization. The non-conjugated diene alcohol, (E)-octa-3,7-dien-1-ol (2), was synthesized according to our previous report [23]. We employed the basic reaction condition of reagents and halide source reported by Liu et al [26].…”
Section: Resultsmentioning
confidence: 99%
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“…Matsumoto and co-workers reported a Lewis acid-mediated Prins cyclization between an alcohol 278 bearing a nonconjugated diene moiety and an aldehyde 277 with alkyl or aryl substituent in presence of BF 3 ·Et 2 O and TMSCl at −40 °C to afford corresponding fluorinated bicyclic compound 284 [ 108 ]. A catalytic amount of TMSCl generates TMS-protected alcohol 279 and HCl.…”
Section: Reviewmentioning
confidence: 99%