1999
DOI: 10.1039/a902414j
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Diastereoselective nucleophilic additions to vinyl phosphine oxides

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Cited by 19 publications
(6 citation statements)
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“…To simplify purification, the cycloalkenyl phosphine was characterised as the phosphine oxide 13 , by using an oxidative work‐up. Further chirality and functionality was introduced into cycloalkenyl phosphine oxide 13 through epoxidation with lithium hydroperoxide48 to give a very stable single diastereoisomeric epoxide 14 (78% yield). The relative stereochemistry at the new chiral centres was readily determined from the vicinal proton and phosphorus coupling constants (15.2 and 5.2 Hz), confirming that the phosphorus atom was in an axial position 49.…”
Section: Resultsmentioning
confidence: 99%
“…To simplify purification, the cycloalkenyl phosphine was characterised as the phosphine oxide 13 , by using an oxidative work‐up. Further chirality and functionality was introduced into cycloalkenyl phosphine oxide 13 through epoxidation with lithium hydroperoxide48 to give a very stable single diastereoisomeric epoxide 14 (78% yield). The relative stereochemistry at the new chiral centres was readily determined from the vicinal proton and phosphorus coupling constants (15.2 and 5.2 Hz), confirming that the phosphorus atom was in an axial position 49.…”
Section: Resultsmentioning
confidence: 99%
“…In our case, the system is perhaps disturbed by the phosphonate oxygen atoms, which might also chelate the lithium ion of the intermediate, [29] as shown for compound 17 ( Figure 1). In our case, the system is perhaps disturbed by the phosphonate oxygen atoms, which might also chelate the lithium ion of the intermediate, [29] as shown for compound 17 ( Figure 1).…”
Section: Scheme 4 Alkylation Of β-Amidobenzenementioning
confidence: 68%
“…17 (3-Hydroxypent-1-en-1-yl)diphenylphosphine Oxide [3k (E + Z)]. 18 White solid. 1 H NMR: δ (ppm) 7.68−7.59 (m, 4H, E + Z), 7.49−7.34 (m, 6H, E + Z), 6.82−6.67 (m, 1H, E + Z), 6.49 (ddd, J 1 = 2.0 Hz, J 2 = 16.8 Hz, J 3 = 24.8 Hz, E), 6.08 (ddd, J 1 = 1.6 Hz, J 2 = 13.6 Hz, J 3 = 25.2 Hz, Z), 5.39 (b, 1H, Z), 4.52−4.46 (m, 1H, Z), 4.22− 4.20 (m, 1H, E), 1.66−1.47 (m, 1H, E + Z), 0.89 (t, J = 7.2 Hz, E + Z).…”
Section: ■ Experimental Sectionmentioning
confidence: 99%