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Volumn 3, Issue 20, 2005, Pages 3734-3748

Chirality transfer in the aza-[2,3]-Wittig sigmatropic rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; NEGATIVE IONS; OLEFINS;

EID: 27744570350     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b510756c     Document Type: Article
Times cited : (18)

References (63)
  • 37
    • 27744477745 scopus 로고    scopus 로고
    • note
    • -1, retention times (R)-6b 7.5 mins, (S)-6b 8.4 mins. From optical rotation data for the single enantiomers of 5a, 3a and 2a we assumed no racemisation occurred as the route was identical to that for the synthesis of 6b and this was verified by later analysis of similar series.
  • 38
    • 27744442831 scopus 로고    scopus 로고
    • note
    • -1, retention times for (E)-7b 29.0 mins and 31.2 mins.
  • 40
    • 27744595704 scopus 로고    scopus 로고
    • note
    • This temperature is from our observations on attempted enantioselective aza-[2,3]-Wittig rearrangements with chiral benzylic anions. See ref. 3.
  • 48
    • 27744442976 scopus 로고    scopus 로고
    • note
    • 2O, in the presence of DMAP and higher boiling DMF.
  • 49
    • 27744470260 scopus 로고    scopus 로고
    • note
    • -1, retention times for (R)-9a 14.2 mins, (S)-9a 16.0 mins and (S)-9b 11.6, (R)-9b 16.2.
  • 52
    • 27744517057 scopus 로고    scopus 로고
    • note
    • -1, retention times (E,S)-13b 59.7 mins and (E,R)-13b 63.6 mins.
  • 57
    • 27744510939 scopus 로고    scopus 로고
    • note
    • The corresponding TBS protected serieswas synthesised, but this suffered from a difficult selective Boc deprotection step that proceeded in only 39% yield.
  • 58
    • 27744473180 scopus 로고    scopus 로고
    • note
    • -1, retention times for (S)-16 18.4, (R)-16 24.0.
  • 59
    • 27744496687 scopus 로고    scopus 로고
    • note
    • -1, retention times (E,S)-17 8.4 mins, (E,S)-17 13.3 mins.
  • 60
    • 27744594537 scopus 로고    scopus 로고
    • note
    • -1, retention times (S)-18 9.9 mins, (R)-18 19.0 mins.
  • 61
    • 27744550300 scopus 로고    scopus 로고
    • note
    • 3).
  • 62
    • 27744487735 scopus 로고    scopus 로고
    • note
    • -1, retention times (E,R)-19 14.6 mins, (E,S)-19 16.1 mins.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.