Synthesis of enantiopure cyclopentitols and aminocyclopentitols mediated by oxyselenenylation of cyclopentene with (R,R)-hydrobenzoin

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6471-6474

  Kim, Kwan Soo ^a   Park II, Jong ^a   Ding, Pingyu ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINOCYCLOPENTITOL; BENZOIN; CYCLOPENTANETETROL; CYCLOPENTANETRIOL; CYCLOPENTENE DERIVATIVE; CYCLOPENTITOL; NATURAL PRODUCT; OXYSELENIDE; SELENIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032171296     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01377-X     Document Type: Article

References (23)

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13. 7. Other selenium reagents such as PhSeCl, PhSeBr, and PhSeOTf frequently generated the undesired haloselenide or hydroxyselenide.
14. 3) δ 1.73-1.86 (m, 1 H), 1.95-2.09 (m, 1 H), 2.18-2.28 (m, 1 H), 2.43-2.57 (m, 1 H), 3.61 (s, 1 H), 4.36 and 4.64 (ABq, J = 8.3 Hz, 2 H), 4.56-4.60 (m, 1 H), 5.98-6.02 (m, 1 H), 6.08-6.12 (m, 1 H), 7.05-7.10 (m, 4 H), 7.17-7.30 (m, 6 H). All new compounds gave satisfactory spectroscopy and/or microanatytical data.
15. 10. Unlike the oxyselenenylation of cyclopentene at the first step, N-PSP gave a poor result in the intramolecular oxyselenenylation.
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18. 13. Although selenide 3 could be isolated as a pure form, a substantial amount of 3 was lost during purification by column chromatography on silica gel.
19. 3) 5 2.35-2.42 (m, 1 H), 2.88-2.94 (m, 1 H), 4.29 (d, J = 8.7 Hz, 1 H), 4.33-4.45 (m, 1 H), 4.48-4.56 (m, 1 H), 4.58 (d, J = 8.7 Hz, 1 H), 5.92-5.98 (m, 1 H), 6.13-6.19 (m, 1 H), 6.91-7.10 (m, 10 H).
20. 15. Pauslen, H.; Brauer, O. Chem. Ber. 1977, 110, 331.
21. 1H NMR (DMSO) δ 1.75 (brs, 2 H), 3.64 (brs, 2 H), 3.94 (brs, 2 H) 4.31 (s, 2 H), 4.66 (s, 2 H).
22. 3) δ 3.76-3.84 (m, 2 H), 4.00-4.08 (m, 2 H), 4.29 (dd, J = 4.7, 0.9 Hz, 1 H), 4.35 and 4.45 (ABq, J = 8.9 Hz, 2 H), 4.64 and 4.70 (ABq, J = 12.3 Hz, 2 H), 4.90 (dd, J = 7.8, 4.7 Hz, 1 H), 5.05 (t, J = 4.7 Hz, 1 H), 6.83-7.42 (m, 20 H).
23. 3) δ 3.01 (brs, 1 H), 3.09 (s, 3 H), 3.45 (s. 3 H), 3.68 (d, J = 4.2 Hz, 1 H), 4.07-4.21 (m, 2 H), 4.40 (dd, J = 9.5, 4.8 Hz, 1 H), 4.49 and 4.78 (ABq, J = 9.2 Hz, 2 H), 5.65 (dd, J = 9.5, 7.2 Hz, 1 H), 6.97-7.06 (m, 4 H), 7.15-7.25 (m, 6 H).