메뉴 건너뛰기




Volumn 125, Issue 12, 2005, Pages 899-925

Development of useful reactions based on the novel reactivities of allenic compounds and their application to tandem cyclizations

Author keywords

Allene; Aziridines; Heterocycles; Medium sized ring; Palladium; Tandem reaction

Indexed keywords

ALCOHOL; ALLENE DERIVATIVE; AZIRIDINE DERIVATIVE; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; PYRROLIDINE DERIVATIVE;

EID: 28544437220     PISSN: 00316903     EISSN: 13475231     Source Type: Journal    
DOI: 10.1248/yakushi.125.899     Document Type: Review
Times cited : (9)

References (183)
  • 12
    • 26444463162 scopus 로고    scopus 로고
    • eds. by Krause N., Hashmi A. S. K., Wiley-VCH, Weinheim
    • Ohno H., Nagaoka Y., Tomioka K., "Modern Allene Chemistry," Vol. 1, eds. by Krause N., Hashmi A. S. K., Wiley-VCH, Weinheim, 2004, pp. 141-181.
    • (2004) Modern Allene Chemistry , vol.1 , pp. 141-181
    • Ohno, H.1    Nagaoka, Y.2    Tomioka, K.3
  • 13
    • 0000220284 scopus 로고
    • eds. by Paquette L. O., John Wiley & Sons, Inc.
    • Lipshutz B. H., Sengupta S., "Organic Reactions," Vol. 42, eds. by Paquette L. O., John Wiley & Sons, Inc., 1992, p. 135.
    • (1992) Organic Reactions , vol.42 , pp. 135
    • Lipshutz, B.H.1    Sengupta, S.2
  • 14
    • 0002032635 scopus 로고
    • ed. by Taylor R. J. K., Oxford University Press, London
    • Ibuka T., Yamamoto Y., "Organocopper Reagents," ed. by Taylor R. J. K., Oxford University Press, London, 1994, pp. 143-158.
    • (1994) Organocopper Reagents , pp. 143-158
    • Ibuka, T.1    Yamamoto, Y.2
  • 67
    • 85039350732 scopus 로고    scopus 로고
    • see ref 7
    • 3-allylpalladium complexes are relatively more stable than other isomers, even if the central carbon of the allyl group is substituted by an aryl group. For example, see ref 7).
  • 68
    • 85039347247 scopus 로고    scopus 로고
    • note
    • Upon exposure of a diastereomixture of 44b and 45b (44b:45b=10:90) to the cyclization conditions at 70°C for 4 h, an isomerized mixture was obtained in 53% yield (44b:45b =60:40). However, this palladium-catalyzed isomerization cannot explain the observed cis selectivity in DMF (44:45=100:0).
  • 80
    • 0037006835 scopus 로고    scopus 로고
    • A palladium (II)-catalyzed domino cyclization of allenynes in the presence of LiBr under oxygen at atmospheric pressure was recently reported: Alcaide B., Almendros P., Aragoncillo C., Chem. Eur. J., 8, 1719-1729 (2002).
    • (2002) Chem. Eur. J. , vol.8 , pp. 1719-1729
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3
  • 81
    • 0000810091 scopus 로고    scopus 로고
    • Yamamoto and co-workers reported that palladium-catalyzed carbonylative tandem cyclization of an allenene that contains an allyl acetate moiety in the presence of carbon monoxide afforded tetracyclic product in 22% yield, although it is only an isolated example: Doi T., Yanagisawa A., Nakanishi S., Yamamoto K., Takahashi T., J. Org. Chem., 61, 2602-2603 (1996).
    • (1996) J. Org. Chem. , vol.61 , pp. 2602-2603
    • Doi, T.1    Yanagisawa, A.2    Nakanishi, S.3    Yamamoto, K.4    Takahashi, T.5
  • 127
    • 85039354903 scopus 로고    scopus 로고
    • note
    • As shown in Chart 10, the cis cyclization to give 121 (Chart 14) would be the predominant process over the trans cyclization.
  • 132
    • 16244408580 scopus 로고    scopus 로고
    • eds. by Krause N., Hashmi A. S. K., Wiley-VCH, Weinheim
    • Ma S., "Modern Allene Chemistry," Vol. 2, eds. by Krause N., Hashmi A. S. K., Wiley-VCH, Weinheim, 2004, pp. 614-619.
    • (2004) Modern Allene Chemistry , vol.2 , pp. 614-619
    • Ma, S.1
  • 150
    • 85039358531 scopus 로고    scopus 로고
    • see: ref 19
    • The starting amino alcohols 129 and 132 were readily prepared from natural amino acids through alkynylation of the corresponding aldehydes, see: ref 19).
  • 151
    • 85039348399 scopus 로고    scopus 로고
    • note
    • The computational investigations were conducted by the B3LYP density functional calculations together with the 6-31+G(d) basis set and the Onsager solvation model.
  • 168
    • 85039361069 scopus 로고    scopus 로고
    • note
    • The trans-configuration of 169 was determined by NOE analysis as shown below. (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.