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Volumn 62, Issue 16, 2006, Pages 3928-3938

Synthesis of chiral allenes from ynamides through a highly stereoselective Saucy-Marbet rearrangement

Author keywords

Axial chirality; Chiral allenes; Saucy Marbet rearrangement; Sibi and evans' auxiliaries; Ynamides

Indexed keywords

4 NITROBENZENESULFONIC ACID; ALCOHOL DERIVATIVE; AMIDE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; YNAMIDE DERIVATIVE;

EID: 33645360618     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.087     Document Type: Article
Times cited : (39)

References (83)
  • 17
    • 85030735977 scopus 로고    scopus 로고
    • Also see Ref. 9a,k
    • (b) Also see Ref. 9a,k.
  • 20
    • 85030727896 scopus 로고    scopus 로고
    • note
    • In addition to reviews in Ref. 1, please see papers in this special issue for a range of elegant chemistry employing electron deficient ynamines.
  • 21
    • 17744371152 scopus 로고    scopus 로고
    • For recent reports on the chemistry of ynamides in the last 3 years, see: (a) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5776
    • Dunetz, J.R.1    Danheiser, R.L.2
  • 41
    • 85030729574 scopus 로고    scopus 로고
    • see Refs. 1 and 2
    • (u) For many other contributions before 2001, see Refs. 1 and 2.
  • 53
    • 0000217402 scopus 로고
    • Claisen Rearrangement; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For reviews, see: (a) Wipf, P. In Claisen Rearrangement; Trost, B. M., Fleming, I., Eds.; Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 5, p 827.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 827
    • Wipf, P.1
  • 79
    • 85030730670 scopus 로고    scopus 로고
    • See Ref. 15
    • Stereochemistry at C2 of the major isomers was assigned based on related Claisen rearrangement using allyl alcohols. See Ref. 15. Attempts to gain crystal structures failed, and isomers with moderate ratios are also difficult to separate.
  • 80
    • 85030736555 scopus 로고    scopus 로고
    • note
    • Allene 40 was obtained in 67% as a single isomer from the reaction of ynamide (R)-10 with chiral propargyl alcohol (S)-35.
  • 81
    • 33845282438 scopus 로고
    • and see also page 7925
    • Obtained via CBS reductions of their respective corresponding ketones: Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551 and see also page 7925.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5551
    • Corey, E.J.1    Bakshi, R.K.2    Shibata, S.3
  • 82
    • 85030733470 scopus 로고    scopus 로고
    • note
    • 2 groups.
  • 83
    • 85030734815 scopus 로고    scopus 로고
    • note
    • 2=c-hex.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.