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Volumn 131, Issue 1, 2009, Pages 14-15

AcOLeDMAP and BnOLeDMAP: Conformationally restricted nucleophilic catalysts for enantioselective rearrangement of indolyl acetates and carbonates

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL CATALYST; ELECTRONWITHDRAWING; ENANTIOSELECTIVE; OXINDOLES;

EID: 62649147050     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805541u     Document Type: Article
Times cited : (126)

References (24)
  • 15
    • 38349156051 scopus 로고    scopus 로고
    • (c)Wurz, R. P. Chem. Rev. 2007, 107, 5570.
    • (2007) Chem. Rev , vol.107 , pp. 5570
    • Wurz, R.P.1
  • 16
    • 33644747186 scopus 로고    scopus 로고
    • For other examples of chiral nucleophile eatalvzed carboxvl rearrangements, see: a
    • For other examples of chiral nucleophile eatalvzed carboxvl rearrangements, see: (a) Nguyen, H. V.: Butler. D. C. D.; Richards. C. J. Qrg. Lett. 2006, 8, 769.
    • (2006) Qrg. Lett , vol.8 , pp. 769
    • Nguyen, H.V.1    Butler, D.C.D.2    Richards, C.J.3
  • 18
    • 67849132038 scopus 로고    scopus 로고
    • The use of less hindered or more basic amines led to nonselective oxindole acetvlation as did less reactive acetyl donors
    • The use of less hindered or more basic amines led to nonselective oxindole acetvlation as did less reactive acetyl donors.
  • 20
    • 67849098705 scopus 로고    scopus 로고
    • Enantiopurity remained the same upon resubjecting oxindole 15b to the reaction conditions, ruling out a reversible reaction.
    • Enantiopurity remained the same upon resubjecting oxindole 15b to the reaction conditions, ruling out a reversible reaction.
  • 22
    • 67849112860 scopus 로고    scopus 로고
    • The oxazoline is formed with retention, suggesting that ester cleavage to the alcohol may be the initiating event. Decomposition of catalyst 12b was not detected in any of the analogous indolyl actetate rearrangements.
    • The oxazoline is formed with retention, suggesting that ester cleavage to the alcohol may be the initiating event. Decomposition of catalyst 12b was not detected in any of the analogous indolyl actetate rearrangements.
  • 23
    • 84869567017 scopus 로고    scopus 로고
    • 3SnH. Oxindoles 22 and 24a have the opposite sense of optical rotation compared to 16 and 18, The chemical correlation of 22a with 24a also supports the analogies used to assign the absolute configurations of 16.
    • 3SnH. Oxindoles 22 and 24a have the opposite sense of optical rotation compared to 16 and 18, The chemical correlation of 22a with 24a also supports the analogies used to assign the absolute configurations of 16.
  • 24
    • 67849134667 scopus 로고    scopus 로고
    • Using 13b in place of 12b for Table 2, entry 1, affords the same major enantiomer of 16a 77% ee; E. McGreevy, unpublished results
    • Using 13b in place of 12b for Table 2, entry 1, affords the same major enantiomer of 16a (77% ee; E. McGreevy, unpublished results).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.