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Volumn , Issue 15, 2009, Pages 2634-2645

Stereoselective olefination reactions promoted by Rieke manganese

Author keywords

, unsaturated esters; , unsaturated amides; Elimination reactions; Manganese; Metalation; Stereoselectivity

Indexed keywords

DIRECT SYNTHESIS; ELIMINATION REACTION; ELIMINATION REACTIONS; HIGH YIELD; METALATION; OLEFINATION; OLEFINATION REACTION; STEREO-SELECTIVE; UNSATURATED ESTERS;

EID: 69749095248     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216880     Document Type: Review
Times cited : (13)

References (93)
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    • No special precaution is required due to the low toxicity of manganese and manganese salts obtained after the aqueous work-up of organomanganese reactions, see
    • No special precaution is required due to the low toxicity of manganese and manganese salts obtained after the aqueous work-up of organomanganese reactions, see: Cahiez, G. An. Quim. 1995, 91, 561.
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    • note
    • Aldrich catalogue (2009-2010): manganese powder (325 mesh): 250 g = 44 €.
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    • For some recent synthetic applications of manganese in organic synthesis, see
    • For some recent synthetic applications of manganese in organic synthesis, see: Concellón, J. M.; Rodríguez-Solla, H.; del Amo, V. Chem. Eur. J. 2008, 14, 10184.
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    • For recent synthesis of α,β-unsaturated amides, see: (a)
    • For recent synthesis of α,β-unsaturated amides, see: (a) Park, J. H.; Kim, S. Y.; Kim, S. M.; Chung, Y. K. Org. Lett. 2007, 9, 2465.
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    • Manganese(II) enolates and related species have been proposed as intermediates in other manganese-promoted transformations: (a)
    • Manganese(II) enolates and related species have been proposed as intermediates in other manganese-promoted transformations: (a) Dessole, G.; Bernardi, L.; Bonini, B. F.; Capitò, E.; Fochi, M.; Herrera, R. P.; Ricci, A.; Cahiez, G. J. Org. Chem. 2004, 69, 8525.
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    • Similar transition state models have been proposed to explain the selectivity in other Mn(II)-promoted reactions
    • Similar transition state models have been proposed to explain the selectivity in other Mn(II)-promoted reactions: Oshima, K. J. Organomet. Chem. 1999, 575, 1.
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    • 2, see: (a) Takai, K. Org. React. 2004, 64, 253.
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    • Only one example (ethyl 3-phenylprop-2-enoate) has been synthesized using a sequential reaction of ethyl dibromoacetate and benzaldehyde promoted by Fe(0)
    • (b) Only one example (ethyl 3-phenylprop-2-enoate) has been synthesized using a sequential reaction of ethyl dibromoacetate and benzaldehyde promoted by Fe(0): Falk, J. R.; Bejot, D. K.; Bandyopadhyay, A.; Joseph, S.; Mioskowski, C. J. Org. Chem. 2006, 71, 8178.
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    • note
    • When the minor diastereoisomer was not observed the E/Z ratio was assigned >98:2.
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    • The coupling constant between the olefinic protons of compounds 5 ranging between J = 14.9 and 15.4 Hz were in accordance with the average literature values: John Wiley & Sons: New York
    • The coupling constant between the olefinic protons of compounds 5 ranging between J = 14.9 and 15.4 Hz were in accordance with the average literature values: Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. In Spectrometric Identification of Organic Compounds; John Wiley & Sons: New York, 1991.
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    • Wittig reactions carried out with enolizable carbonyl compounds can generate alkenes in very low yields
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.