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Volumn 125, Issue 49, 2003, Pages 14992-14993

Asymmetric Intermolecular Pauson-Khand Reactions of Unstrained Olefins: The (o-Dimethylamino)phenylsulfinyl Group as an Efficient Chiral Auxiliary

Author keywords

[No Author keywords available]

Indexed keywords

5 SULFINYL 2 CYCLOPENTENONE DERIVATIVE; ALKENE DERIVATIVE; ANTIBIOTIC AGENT; CYCLOPENTENONE DERIVATIVE; PENTENOMYCIN I; PHENYL GROUP; SULFOXIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 0344236126     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038491l     Document Type: Article
Times cited : (69)

References (28)
  • 14
    • 0000257390 scopus 로고
    • Krafft et al. demonstrated that sulfur and nitrogen coordination to cobalt improves the reactivity and regioselectivity in intermolecular PKR of unstrained alkenes: Krafft, M. E.; Juliano, C. A.; Scott, I. A.; Wright, C.; McEachin, M. D. J. Am. Chem. Soc. 1991, 113, 1693-1703.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1693-1703
    • Krafft, M.E.1    Juliano, C.A.2    Scott, I.A.3    Wright, C.4    McEachin, M.D.5
  • 15
    • 0037119779 scopus 로고    scopus 로고
    • For the use of pyridylsilyl as directing group in the intermolecular Ru-catalyzed PKR, see: Itami, K.; Mitsudo, K.; Yoshida, J. Angew. Chem., Int. Ed. 2002, 41, 3481-3484.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3481-3484
    • Itami, K.1    Mitsudo, K.2    Yoshida, J.3
  • 21
    • 0033165960 scopus 로고    scopus 로고
    • In contrast, the intermolecular PKR of electron-poor alkenes, such as methyl acrylate, is completely regioselective: Ahmar, M.; Antras, F.; Cazes, B. Tetrahedron Lett. 1999, 40. 5503-5506.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5503-5506
    • Ahmar, M.1    Antras, F.2    Cazes, B.3
  • 22
    • 0032558144 scopus 로고    scopus 로고
    • For the use of the o-(dimethylamino)phenylsulfinyl group as chiral auxiliary in asymmetric Heck reactions, see: Díaz Buezo, N.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7129-7130
    • Díaz Buezo, N.1    Alonso, I.2    Carretero, J.C.3
  • 23
    • 0345471334 scopus 로고    scopus 로고
    • note
    • The stereochemical assignment of the diastereomers 2-9 (A + B) was first tentatively established by NMR and unequivocally confirmed in the case of 3A by X-ray diffraction.
  • 24
    • 0344177464 scopus 로고    scopus 로고
    • Van Eldik, R., Klaerner, F.-G., Eds.; Wiley-VCH: Weinheim, Germany
    • For a review on the use of high pressure on organometallic reactions, see: Reiser, O. In High-Pressure Chemistry; Van Eldik, R., Klaerner, F.-G., Eds.; Wiley-VCH: Weinheim, Germany, 2002; pp 223-238.
    • (2002) High-Pressure Chemistry , pp. 223-238
    • Reiser, O.1
  • 27
    • 0345040120 scopus 로고    scopus 로고
    • note
    • As a second example of the lack of racemization at sulfur in the asymmetric version of this PKR, adduct (5S,SR)-7A was obtained in >99% ee from enantiopure vinyl sulfoxide (R)-1f.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.