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Volumn 13, Issue 4, 2007, Pages 1326-1331

Cyclopropanation of enantiopure metal alkenyl carbenes with 2-methoxyfuran: A practical route to carboxycyclopropylglycine precursors

Author keywords

Asymmetric synthesis; Carbenes; Chiral pool; Cyclopropanation; Diastereoselectivity

Indexed keywords

AROMATIC HYDROCARBONS; DERIVATIVES; ISOMERS; REACTION KINETICS; STEREOCHEMISTRY;

EID: 33846635964     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601332     Document Type: Article
Times cited : (16)

References (33)
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    • and references therein
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    • For a very interesting review on stereoselective cyclopropane formation see
    • For a very interesting review on stereoselective cyclopropane formation see: H. Lebel, J. F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050.
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    • Complexes 1a and 1b are prepared from readily available and cheap starting materials, such as (R)-2,3-O-isopropylidene-D-glyceraldehyde and (S)-2,4-O-benzylidene-3-deoxyerythrose, respectively. See: J. Barluenga, N. Panday, J. Santamaría, A. de Prado, M. Tomás, ARKIVOC 2003, 576-583.
    • Complexes 1a and 1b are prepared from readily available and cheap starting materials, such as (R)-2,3-O-isopropylidene-D-glyceraldehyde and (S)-2,4-O-benzylidene-3-deoxyerythrose, respectively. See: J. Barluenga, N. Panday, J. Santamaría, A. de Prado, M. Tomás, ARKIVOC 2003, 576-583.
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    • For other diastereoselective cyclopropanations of alkenylcarbene complexes see: a
    • For other diastereoselective cyclopropanations of alkenylcarbene complexes see: a) With chloromethylllithium: J. Barluenga, P. L. Bernad, Jr., J. M. Concellón, A. Piñera-Nicolás, S. García-Granda, J. Org. Chem. 1997, 62, 6870-6875;
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    • with lithiated epoxides: V. Capriati, S. Florio, R. Luisi, F. M. Perna, J. Barluenga, J. Org. Chem. 2005, 70, 5852-5858.
    • b) with lithiated epoxides: V. Capriati, S. Florio, R. Luisi, F. M. Perna, J. Barluenga, J. Org. Chem. 2005, 70, 5852-5858.
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    • Selected reviews: a F. Z. Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, New York, 1999;
    • Selected reviews: a) F. Z. Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, New York, 1999;
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    • for a review in cyclopropyl Fischer carbene complexes see: J. W. Herndon, Curr. Org. Chem. 2003, 7, 329-352.
    • d) for a review in cyclopropyl Fischer carbene complexes see: J. W. Herndon, Curr. Org. Chem. 2003, 7, 329-352.
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    • For a similar approach see reference [10b
    • For a similar approach see reference [10b].
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    • For a different approach using a sulfur ylide see: a
    • For a different approach using a sulfur ylide see: a) D. Ma, Y. Cao, Y. Yang, D. Cheng, Org. Lett. 1999, 1, 285-287;
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    • 2 at room temperature for a long time results in the recovery of the starting materials.
    • 2 at room temperature for a long time results in the recovery of the starting materials.
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    • A few methods are available for the synthesis of optically active cyclopropanecarbaldehydes by ring-forming reactions. For an elegant piece of work on the enantioselective organocatalytic synthesis of cyclopropanecarbaldehydes see: a R. K. Kunz, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3240-3241;
    • A few methods are available for the synthesis of optically active cyclopropanecarbaldehydes by ring-forming reactions. For an elegant piece of work on the enantioselective organocatalytic synthesis of cyclopropanecarbaldehydes see: a) R. K. Kunz, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3240-3241;
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    • for access to enantiopure cyclopropanecarbadehydes starting from hydroxyalquenyl carbamates see
    • b) for access to enantiopure cyclopropanecarbadehydes starting from hydroxyalquenyl carbamates see: R. Kalkofen, S. Brandau, B. Wibbeling, D. Hoppe, Angew. Chem. 2004, 116, 6836;
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    • reference [3] and references therein.
    • c) reference [3] and references therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.