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Volumn 74, Issue 5, 2009, Pages 2193-2196

Enyne metathesis/Brønsted acid-promoted heterocyclization

Author keywords

[No Author keywords available]

Indexed keywords

ENYNE METATHESIS; HETEROCYCLE; HETEROCYCLIZATION; IN-SITU; NITROGEN HETEROCYCLES; ONE POTS;

EID: 64249086360     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802582k     Document Type: Article
Times cited : (28)

References (35)
  • 1
    • 84869271067 scopus 로고    scopus 로고
    • Nitrogen Heterocycles: (a) Bäckvall, J. E.; Nyström, J. E. J. Chem. Soc., Chem. Commun. 1981, 5, 9-61.
    • Nitrogen Heterocycles: (a) Bäckvall, J. E.; Nyström, J. E. J. Chem. Soc., Chem. Commun. 1981, 5, 9-61.
  • 13
    • 13244289965 scopus 로고    scopus 로고
    • In this case, only E-4A was detected. In the cross metathesis step with simple alkenes, longer periods of heating give primarily the E-isomer: (a) Giessert, A. J.; Diver, S. T. J. Org. Chem. 2005, 70, 1046-1049.
    • In this case, only E-4A was detected. In the cross metathesis step with simple alkenes, longer periods of heating give primarily the E-isomer: (a) Giessert, A. J.; Diver, S. T. J. Org. Chem. 2005, 70, 1046-1049.
  • 15
    • 64249104874 scopus 로고    scopus 로고
    • Similar studies were conducted with pure, E-4B: 4 equiv TFA promoted the cyclization 100% conversion, 73% isolated, However, in the one-pot reaction, 4 equiv of TFA did not result in full conversion of the intermediate 1,3-diene. Since excess alkene was still present, higher amounts of acid were needed, see ref 8
    • Similar studies were conducted with pure, E-4B: 4 equiv TFA promoted the cyclization (100% conversion, 73% isolated). However, in the one-pot reaction, 4 equiv of TFA did not result in full conversion of the intermediate 1,3-diene. Since excess alkene was still present, higher amounts of acid were needed, see ref 8.
  • 19
    • 64249096178 scopus 로고    scopus 로고
    • Interestingly, the He study (ref 7) reported intermolecular 1,2-hydroamination of unactivated alkenes. In the present case, it is likely that some loss of material is due to addition reactions to remaining 1-hexene.
    • Interestingly, the He study (ref 7) reported intermolecular 1,2-hydroamination of unactivated alkenes. In the present case, it is likely that some loss of material is due to addition reactions to remaining 1-hexene.
  • 20
    • 64249103075 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 23
    • 0023779454 scopus 로고    scopus 로고
    • 1,3 strain was invoked in N-acyl piperidinone to explain diastereoselection during conjugate addition reactions: (a) Brown, J. D.; Foley, M. A.; Comins, D. L J. Org 1988, 110, 7445-7447. For similar reasons, the N-tosyl group in a piperidine ring system causes the 2-substituent to occupy an axial position.
    • 1,3 strain was invoked in N-acyl piperidinone to explain diastereoselection during conjugate addition reactions: (a) Brown, J. D.; Foley, M. A.; Comins, D. L J. Org 1988, 110, 7445-7447. For similar reasons, the N-tosyl group in a piperidine ring system causes the 2-substituent to occupy an axial position.
  • 26
    • 0034051322 scopus 로고    scopus 로고
    • Other ring-rearrangements: Piperidine: a
    • Piperidine: (a) Voigtmann, U.; Blechert, S. Synthesis 2000, 893-898. Other ring-rearrangements:
    • (2000) Synthesis , pp. 893-898
    • Voigtmann, U.1    Blechert, S.2
  • 31
    • 64249085129 scopus 로고    scopus 로고
    • In this case, fewer equivalents of TFA were found to promote the cyclization. Carbene 1 also promoted this metathesis.
    • In this case, fewer equivalents of TFA were found to promote the cyclization. Carbene 1 also promoted this metathesis.
  • 33
    • 60949091784 scopus 로고    scopus 로고
    • Use of methylene cyclobutane in enyne metathesis: Clark, D. C.; Karnofel, W.; Basile, B.; Diver, S. T. Org. Lett. 2008, 10, 4927-4929.
    • Use of methylene cyclobutane in enyne metathesis: Clark, D. C.; Karnofel, W.; Basile, B.; Diver, S. T. Org. Lett. 2008, 10, 4927-4929.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.