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Tetrahedron Letters
Volumn 35, Issue 4, 1994, Pages 543-546
A comparison of ligands proposed for the asymmetric dihydroxylation
Author keywords

[No Author keywords available]
Indexed keywords

PHTHALAZINE DERIVATIVE; PYRIDAZINE DERIVATIVE; QUINIDINE DERIVATIVE; QUINOLINE DERIVATIVE;
EID: 0028274141     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)75833-3     Document Type: Article
Times cited : (25)
References (13)
  • 3
    • 84913005931 scopus 로고    scopus 로고
    • Both of the ligands in question (2a and 3a) were prepared and tested by the Sharpless group at MIT, as part of the general ligand screening process. They were subsequently rejected due to the observed superiority of the phthalazine class of ligands in virtually all applications of the AD process: Hartung, J., Jeong, K.-S., Sharpless, K.B. unpublished results. (Pyridazine ligands 2a and 2b are included in MIT's U.S. Pat. Appl. No. 077/775, 683, Oct. 10, 1991.)
  • 7
    • 84912991312 scopus 로고    scopus 로고
    • Since the enantioselectivities obtained with dihydroquinidylpyridazine 2a and the phthalazine 1a are very close for most substrates, cost considerations may make this pyridazine attractive for β-face selective AD on a large scale.
  • 8
    • 84989588393 scopus 로고
    • Enantioselective Synthesis of Both Enantiomers of 7,7-Dimethyl-6,8-dioxa-bicyclo[3.2.1]octane via Regioselective Asymmetric Dihydroxylation
    • (1993) Synlett , pp. 47
    • Crispino1    Sharpless2
  • 10
    • 84912980689 scopus 로고    scopus 로고
    • 11 where C is the percent conversion/100 and ee is the enantiomeric excess of the recovered olefin/100, respectively. A relative rate of 10.7 can be calculated with C = 0.60 and ee = 0.88 as reported in ref. 9.
  • 11
    • 8044227965 scopus 로고
    • This equation is an adaptation of one presented by Kagan where the variables have been changed to those most applicable to synthetic problems.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5152
    • Balavoine1    Moradpour2    Kagan3
  • 12
    • 0000909224 scopus 로고
    • 2-TP 3a or DHQD-CLB 4a. This unexpected result is currently under investigation., For examples of kinetic resolution with the phthalazine class of ligands see
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7864
    • VanNieuwenhze1    Sharpless2
  • 13
    • 33751385752 scopus 로고
    • A recent report from these laboratories describes a new class of diphenylpyrimidine ligands which give higher enantioselectivies than phthalazine 1 for terminal olefins, especially those with branching in the substitutent:
    • (1993) J. Org. Chem. , vol.58 , pp. 3785
    • Crispino1    Jeong2    Kolb3    Wang4    Xu5    Sharpless6

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.