A solid-phase version of the Nozaki-Hiyama allylation of aldehydes with supported allylic bromides

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1511-1513

  Breitenstein, Klaus ^a,b   Llebaria, Amadeu ^b   Delgado, Antonio ^a,b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

Allylation; Chromium; Lactones; Solid phase

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALLYL COMPOUND; BROMIDE; GAMMA BUTYROLACTONE DERIVATIVE;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; NOZAKI HIYAMA ALLYLATION; SOLID;

EID: 1642497626     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.017     Document Type: Article

References (24)

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14. 2, and MeOH on a filter funnel, and dried under vacuum. The approximate loading was estimated based on resin weight increase. Aldehydes 2a-d required 3 cycles for complete reaction, weight increase of resins 3a-d was higher than 98% of the theoretical loading. For a similar protocol and a general overview of Baylis-Hilman reactions, see: Patra A., Roy A.K., Joshi B.S., Roy R., Batra S., Bhaduri A.P. Tetrahedron. 59:2003;663-670. and references cited therein.
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16. 2Br).
17. See Ref. [7a].
18. q), 170.3 (CO).
19. 1H NMR data, is in agreement with the postulated mechanism operating for this allylation process. See: Ref. [7d], p 189.
20. Okuda Y., Natatsukasa S., Oshima K., Nozaki H. Chem. Lett. 1985;481-484.
21. Drewes S.E., Hoole R.F.A. Synth. Commun. 15:1985;1067-1074.
22. Furstner A., Shi N.Y. J. Am. Chem. Soc. 118:1996;12349-12357 The Cr catalytic version of the Nozaki-Hiyama reaction was tried in order to prevent spontaneous cyclization cleavage by trapping the reactive Cr-alkoxide intermediate as the corresponding silyl ether. Unfortunately, all attempts were unsuccessful and lactones 7 were also obtained from the filtrates in high yields.
23. 2O 4:1) to give lactones 7 (see Table 1).
24. 2 to avoid spontaneous lactonization has already been reported (see Ref. [15c]).