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Volumn 624, Issue 1-2, 2001, Pages 96-104

Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via ( - )-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation

Author keywords

( ) Sparteine; Chiral carbanions; Cyclocarbolithiation; Kinetic resolution; Lithiated alkyl carbamates

Indexed keywords


EID: 0002611750     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00832-9     Document Type: Article
Times cited : (11)

References (51)
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    • Asymmetric cyclocarbolithiation reactions, using classical approaches to generate the enantioenriched, open-chain lithium intermediate: (a) I. Coldham, R. Hufton, D.J. Snowden, J. Am. Chem. Soc. 118 (1996) 5322.
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    • note
    • The (-)-sparteine complex of lithiomethylindene delivers carbonyl adducts with high enantiomeric excesses, but all attempts to achieve enantioselective alkylations have failed so far [13]. Despite that, (-)-sparteine was used, since better regioselectivities were observed in comparison to the lithium TMEDA complex.
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    • -3, Flack parameter -0.1(3), positional disorder at 011, refined with split positions (0.74(1): 0.26(1)), hydrogens calculated and refined as riding atoms. Data set was collected with an Enraf-Nonius CAD4 diffractometer. Programs used: data collection EXPRESS (Nonius B.V., 1994), data reduction MOLEN (K. Fair, Enraf-Nonius B.V., 1990), structure solution SHELXS-97 (G.M. Sheldrick, Acta Crystallogr., Sect. A 46 (1990) 467), structure refinement SHELXL-97 (G.M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, Universität Freiburg, 1997).
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    • note
    • -1 in favour of the observed reaction path. However, for the sake of simplicity, the ligand (-)-sparteine was removed from the model compounds.
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    • note
    • The configuration and the enantiomeric purity of (-)-18 or of its precursors could not be assessed. In analogy to the cyclopropane 14, the proposed absolute configuration and a high enantiomeric excess are most likely.
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    • The enantiomeric excess could not be determined.
    • The enantiomeric excess could not be determined.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.