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Volumn 11, Issue 15, 2009, Pages 3442-3445

A novel prins cyclization through benzylic/allylic C-H activation

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE; DICHLOROMETHANE; ETHER DERIVATIVE; PYRAN DERIVATIVE;

EID: 68149087631     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901291w     Document Type: Article
Times cited : (59)

References (43)
  • 1
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    • For reviews on the Prins cyclization, see: a
    • For reviews on the Prins cyclization, see: (a) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 52, 505.
    • (1952) Chem. Rev , vol.52 , pp. 505
    • Arundale, E.1    Mikeska, L.A.2
  • 3
    • 0001290261 scopus 로고
    • Trost, B. M, Fleming, I, Heathcock, C. H, Eds, Pergamon Press: New York
    • (c) Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 527-561.
    • (1991) The Prins Reaction and Carbonyl Ene Reactions , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 5
    • 33750057104 scopus 로고    scopus 로고
    • For a recent review on the synthesis of tetrahydropyran rings, see
    • For a recent review on the synthesis of tetrahydropyran rings, see: Santos, S.; Clarke, P. A. Eur. J. Org. Chem. 2006, 2045.
    • (2006) Eur. J. Org. Chem , pp. 2045
    • Santos, S.1    Clarke, P.A.2
  • 6
    • 33646461681 scopus 로고    scopus 로고
    • For recent work on Prins cyclization methodology, see: a
    • For recent work on Prins cyclization methodology, see: (a) Miranda, P. O.; Ramirez, M. A.; Martin, V. S.; Padrón, J. I. Org. Lett. 2006, 8, 1633.
    • (2006) Org. Lett , vol.8 , pp. 1633
    • Miranda, P.O.1    Ramirez, M.A.2    Martin, V.S.3    Padrón, J.I.4
  • 26
    • 33645674829 scopus 로고    scopus 로고
    • For recent reviews and commentary, see: a
    • For recent reviews and commentary, see: (a) Godula, K.; Sames, D. Science 2006, 312, 67.
    • (2006) Science , vol.312 , pp. 67
    • Godula, K.1    Sames, D.2
  • 38
    • 68149127937 scopus 로고    scopus 로고
    • When 4 Å MS was not used to remove water that might be present in the reaction mixture, an amount of p-methoxylbenzaldehyde was observed by TLC
    • When 4 Å MS was not used to remove water that might be present in the reaction mixture, an amount of p-methoxylbenzaldehyde was observed by TLC
  • 39
    • 26444496462 scopus 로고    scopus 로고
    • and ref 4d. For a recent synthesis of centrolobine via the Prins cyclization, see
    • For a recent synthesis of centrolobine via the Prins cyclization, see: Chan, K.-P.; Loh, T. -P. Org. Lett. 2005, 7, 4491, and ref 4d.
    • (2005) Org. Lett , vol.7 , pp. 4491
    • Chan, K.-P.1    Loh, T.-P.2
  • 42
    • 68149139060 scopus 로고    scopus 로고
    • Allyl transfer processes can lead to a loss in optical activity for Prins cyclization reactions (see the mechanism below). Racemization relies on the presence of water. Direct Prins cyclizations utilizing homoallylic alcohols and aldehydes generate water upon condensation. Segment-coupling Prins cyclizations developed by Rychnovsky's group, however, do not generate water in situ and therefore can be used to avoid racemization.
    • Allyl transfer processes can lead to a loss in optical activity for Prins cyclization reactions (see the mechanism below). Racemization relies on the presence of water. Direct Prins cyclizations utilizing homoallylic alcohols and aldehydes generate water upon condensation. Segment-coupling Prins cyclizations developed by Rychnovsky's group, however, do not generate water in situ and therefore can be used to avoid racemization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.