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Volumn 7, Issue 21, 2005, Pages 4701-4704

Three-component, room temperature crotylation catalyzed by solid-supported Brønsted acid: Enantioselective synthesis of homoallylic carbamates

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CROTYLSILANE; POLYSTYRENE DERIVATIVE; SILANE DERIVATIVE; SULFONIC ACID DERIVATIVE;

EID: 27144438710     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051885s     Document Type: Article
Times cited : (21)

References (36)
  • 2
    • 0038106171 scopus 로고    scopus 로고
    • (b) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 20
    • 15444366213 scopus 로고    scopus 로고
    • Via the in situ condensation of an aldehyde and a secondary TMS ether: (a) Su, Q.; Panek, J. S. Angew. Chem., Int. Ed. 2005, 44, 1223-1225.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1223-1225
    • Su, Q.1    Panek, J.S.2
  • 23
    • 27144550126 scopus 로고    scopus 로고
    • note
    • 4 alone did not promote the reaction.
  • 24
    • 27144535315 scopus 로고    scopus 로고
    • note
    • 3 quench or by filtration through basic solid-phase extraction cartridges.
  • 26
    • 27144436152 scopus 로고    scopus 로고
    • note
    • 2 purge.
  • 27
    • 27144544740 scopus 로고    scopus 로고
    • note
    • 1H NMR coupling constant studies of the oxazolidinone derivatives of such products.
  • 28
    • 0000765299 scopus 로고
    • 4-Anisaldehyde is a poor substrate for generating useful levels of diastereoselectivity in crotylsilane additions. See: Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 6594-6600.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6594-6600
    • Panek, J.S.1    Yang, M.2
  • 29
    • 27144559593 scopus 로고    scopus 로고
    • note
    • R minor = 31.9 min.
  • 30
    • 0343778881 scopus 로고
    • A synclinal transition state has also been invoked for the formation of the syn product; see ref 2b. For a more complete discussion of the acyclic stereocontrol elements of (E)-crotylsilane additions, see: Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1326.
    • (1995) Chem. Rev. , vol.95 , pp. 1293-1326
    • Masse, C.E.1    Panek, J.S.2
  • 31
    • 27144482677 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the crude reaction mixture.
  • 32
    • 27144507289 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis.
  • 33
    • 27144489955 scopus 로고    scopus 로고
    • note
    • Preparations of 1a and 1b that were stored as neat liquids on the order of 1 year at room temperature were used in this paper and produced results indistinguishable with those of freshly prepared reagents.
  • 34
    • 0000650159 scopus 로고
    • Three-component synthesis of homoallylic ethers: (a) Panek, J. S.; Yang, M. J. Org. Chem. 1991, 56, 5755-5758.
    • (1991) J. Org. Chem. , vol.56 , pp. 5755-5758
    • Panek, J.S.1    Yang, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.