메뉴 건너뛰기




Volumn 130, Issue 38, 2008, Pages 12588-12589

Highly enantioselective Diels Alder reactions of Danishefsky type dienes with electron-deficient alkenes catalyzed by Yb(III)-BINAMIDE complexes

Author keywords

[No Author keywords available]

Indexed keywords

1 METHOXY 3 TRIMETHYLSILOXY 1,3 BUTADIENE; 1,3 BUTADIENE; 2 CYCLOHEXENONE; ALKADIENE; CYCLOHEXENE DERIVATIVE; DANISHEFSKY TYPE DIENE; METAL COMPLEX; NATURAL PRODUCT; UNCLASSIFIED DRUG; YTTERBIUM; YTTERBIUM BINAMIDE COMPLEX;

EID: 52449111844     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804430n     Document Type: Article
Times cited : (63)

References (28)
  • 2
    • 0000610534 scopus 로고    scopus 로고
    • In Stereoselective Synthesis, Houben-Weyl
    • 4th ed, Hoffmann, R. W, Mulzer, J, Schaumann, E, Eds, Verlag: Stuttgart
    • (a) Jurezak, J.; Bauer, T.; Chapuis, C. In Stereoselective Synthesis, Houben-Weyl, 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Verlag: Stuttgart, 1996; Vol. E21c, pp 2735.
    • (1996) Helmchen, G , vol.E21c , pp. 2735
    • Jurezak, J.1    Bauer, T.2    Chapuis, C.3
  • 4
    • 0000973795 scopus 로고    scopus 로고
    • Representative examples:(a) Myers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc. 1985, 107, 7776.
    • Representative examples:(a) Myers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc. 1985, 107, 7776.
  • 10
    • 0034675619 scopus 로고    scopus 로고
    • Enantioselective hetero-DA reactions of Danishefsky type diene with aldehydes, see: a
    • Enantioselective hetero-DA reactions of Danishefsky type diene with aldehydes, see: (a) Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 3558
    • Jørgensen, K.A.1
  • 12
    • 0031980938 scopus 로고    scopus 로고
    • For enantioselective hetero-DA reactions of Danishefsky type dienes with imines, see: a
    • For enantioselective hetero-DA reactions of Danishefsky type dienes with imines, see: (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979.
    • (1998) Angew. Chem., Int. Ed , vol.37 , pp. 979
    • Kobayashi, S.1    Komiyama, S.2    Ishitani, H.3
  • 23
    • 52449104549 scopus 로고    scopus 로고
    • Determined by X-ray analysis of compound 7. See Supporting Information.
    • Determined by X-ray analysis of compound 7. See Supporting Information.
  • 24
    • 52449094604 scopus 로고    scopus 로고
    • When the reaction was carried out in the presence of 25 mol% of an achiral Yb(OTf)3-iPr2NEt complex, the exo adduct 4a was obtained exclusively in 63% yield. Thus, the exo selectivity should originate from substrate control. Even when the reaction was carried out at 100°C without any catalyst, a mixture of diastereoisomers was obtained (exolendo, 3:2, The presence of an oxazolidinone unit in the structure of dienophiles is essential for high enantiomeric induction. Results obtained using other chiral ligands with Yb(OTf)3 are shown in the Supporting Information
    • 3 are shown in the Supporting Information.
  • 25
    • 52449113092 scopus 로고    scopus 로고
    • The absolute stereochemistry of 5b was determined to be 4S by comparison of the specific rotation of (S)-4-(hydroxymethyl)cyclohex- 2-enone (11) with the reported value (ref 7). The absolute stereochemistries of 5a and 5c-i were estimated to be 4S by analogy to 5b. See Supporting Information for details.
    • The absolute stereochemistry of 5b was determined to be 4S by comparison of the specific rotation of (S)-4-(hydroxymethyl)cyclohex- 2-enone (11) with the reported value (ref 7). The absolute stereochemistries of 5a and 5c-i were estimated to be 4S by analogy to 5b. See Supporting Information for details.
  • 27
    • 0032538773 scopus 로고    scopus 로고
    • See Supporting Information Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922.
    • See Supporting Information Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922.
  • 28
    • 34547207608 scopus 로고    scopus 로고
    • Recently, an asymmetric Diels-Alder reaction using a Danishefsky type diene has been reported: Ward, D. E.; Shen, J. Org. Lett. 2007, 9, 2843.
    • Recently, an asymmetric Diels-Alder reaction using a Danishefsky type diene has been reported: Ward, D. E.; Shen, J. Org. Lett. 2007, 9, 2843.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.