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Volumn 9, Issue 14, 2007, Pages 2713-2716

Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: Synthesis of (+)-sappanone B

Author keywords

[No Author keywords available]

Indexed keywords

ABROTANONE; ALDEHYDE; BENZOIN; DITERPENE; ETHYLAMINE; TRIAZOLE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 34547424960     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070929p     Document Type: Article
Times cited : (118)

References (31)
  • 12
    • 34547419365 scopus 로고    scopus 로고
    • The (R) configuration of α-ketol 5 was confirmed by X-ray analysis of the corresponding (S)-camphanyl derivative. See ref 1
    • The (R) configuration of α-ketol 5 was confirmed by X-ray analysis of the corresponding (S)-camphanyl derivative. See ref 1.
  • 13
    • 34547474781 scopus 로고    scopus 로고
    • Use of various bases of different strength (KHMDS, KOt-Bu, quinuclidine) was unfruitful, invariably producing 6-9 in 50-70% yield.
    • Use of various bases of different strength (KHMDS, KOt-Bu, quinuclidine) was unfruitful, invariably producing 6-9 in 50-70% yield.
  • 14
    • 0037157115 scopus 로고    scopus 로고
    • For the basicity of imidazol-2-ylidene in, and references cited therein
    • For the basicity of imidazol-2-ylidene in THF, see: Kim, Y.-J.; Streitwieser, A. J. Am. Chem. Soc. 2002, 124, 5757-5761 and references cited therein.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 5757-5761
    • see, T.H.F.1    Kim, Y.-J.2    Streitwieser, A.3
  • 18
    • 34547433934 scopus 로고    scopus 로고
    • The corresponding reaction by using the triazolium salt with the ortho-mono-methylated N-phenyl group [15 mol, Et3N (10 mol , toluene, room temperature] provided a-ketol 5 in poorer selectivity 44, 62% ee
    • 3N (10 mol %), toluene, room temperature] provided a-ketol 5 in poorer selectivity (44%, 62% ee).
  • 23
    • 34547409073 scopus 로고    scopus 로고
    • The origin of the reversal of stereoinduction between biaryl ketoaldehyde and others is under investigation
    • The origin of the reversal of stereoinduction between biaryl ketoaldehyde and others is under investigation.
  • 27
    • 34547488153 scopus 로고    scopus 로고
    • It should be noted that the cyclization by using 3a [15 mol, Et 3N (10 mol , toluene] gave α-ketol (R)-23 in substantially lower yield 24, 92% ee
    • 3N (10 mol %), toluene] gave α-ketol (R)-23 in substantially lower yield (24%, 92% ee).
  • 28
    • 1242273826 scopus 로고    scopus 로고
    • Sodium dodecanethiolate was prepared by mixing dodecanethiol with sodium methoxide (28 wt % in MeOH) followed by evaporation (see the Supporting Information). For odorless thiols and sulfides, see: Nishide, K.; Ohsugi, S.; Miyamoto, T.; Kumar, K.; Node, M. Monatsh. Chem. 2004, 135, 189-200.
    • Sodium dodecanethiolate was prepared by mixing dodecanethiol with sodium methoxide (28 wt % in MeOH) followed by evaporation (see the Supporting Information). For odorless thiols and sulfides, see: Nishide, K.; Ohsugi, S.; Miyamoto, T.; Kumar, K.; Node, M. Monatsh. Chem. 2004, 135, 189-200.
  • 29
    • 34547429208 scopus 로고    scopus 로고
    • For the X-ray analysis of 4-bromobenzoyl derivative 26, see the Supporting Information.
    • For the X-ray analysis of 4-bromobenzoyl derivative 26, see the Supporting Information.
  • 30
    • 0010070090 scopus 로고    scopus 로고
    • Application of 1 onto a commercial silica gel caused a serious tailing of a spot or a band, rendering the assay and purification of 1 extremely difficult. The situation was cleared by the use of oxalated silica gel. For oxalated silica gel, see the Supporting information and; Cameron, D. W.; Riches, A. G. Aust. J. Chem. 1997, 50, 409-424.
    • Application of 1 onto a commercial silica gel caused a serious tailing of a spot or a band, rendering the assay and purification of 1 extremely difficult. The situation was cleared by the use of oxalated silica gel. For oxalated silica gel, see the Supporting information and; Cameron, D. W.; Riches, A. G. Aust. J. Chem. 1997, 50, 409-424.
  • 31
    • 34547401301 scopus 로고    scopus 로고
    • 6-acetone. See the Supporting information.
    • 6-acetone. See the Supporting information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.