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Volumn 43, Issue 44, 2004, Pages 5977-5980

A highly stereoselective addition of the anion derived from α-diazoacetamide to aromatic N-tosylimines

Author keywords

Amino acids; Chiral auxiliaries; Diastereoselectivity; Diazo compounds; Nucleophilic addition

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; BIOSYNTHESIS; DERIVATIVES; NEGATIVE IONS; POLYAMIDES; SYNTHESIS (CHEMICAL);

EID: 9244247270     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460730     Document Type: Article
Times cited : (35)

References (59)
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    • note
    • d) N-(diazoacetyl)oxazolidinone 1d can be easily prepared from the reaction of (S)-(-)-4-benzyl-2-oxazolidinone with triphosgene, followed by treatment with diazomethane, or by deprotonation of (5)-(-)-4-benzyl-2- oxazolidinone acetamide with LDA and diazo transfer from o-nitrophenylsulfonyl azide. See the Supporting Information for details.
  • 38
    • 0039255361 scopus 로고    scopus 로고
    • and references therein
    • The use of HMPA for improving the diastereoselectivity in lithium enolate reactions has been reported; see: E. Juaristi, J. L. León-Romo, Y. Ramírez-Quirós, J. Org. Chem. 1999, 64, 2914, and references therein.
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    • 9244247039 scopus 로고    scopus 로고
    • note
    • a) CCDC-239004 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk);
  • 40
    • 9244221354 scopus 로고    scopus 로고
    • note
    • b) the R configuration was also confirmed by correlating the product 3da with the known compound (2R,3S)-11a. See the Supporting Information.
  • 42
    • 0034678006 scopus 로고    scopus 로고
    • a) C. Palomo, M. Oiarbide, M. C. González-Rego, A. K. Sharma, J. M. García, A. González, C. Landa, A. Linden, Angew. Chem. 2000, 112, 1105; Angew. Chem. Int. Ed. 2000, 39, 1063;
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  • 44
    • 9244233083 scopus 로고    scopus 로고
    • note
    • Although the exact structure of the deprotonated diazoacetyl compound is not known, it should be more reasonable to consider it as a carbanion, in which the negative charge is localized on the diazo-bound carbon atom.
  • 45
    • 9244256493 scopus 로고    scopus 로고
    • ref. [9,10]
    • HMPA has been known to dramatically alter the regio- and/or stereoselectivity in the reaction of lithium enolates with electrophiles; see a) ref. [9,10];
  • 49
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    • Chelated and nonchelated enolates derived from Evans' reagents have been reported to give opposite stereoselectivities in aldol reactions, see: M. A. Walker, C. H. Heathcock, J. Org. Chem. 1991, 56, 5747.
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    • Walker, M.A.1    Heathcock, C.H.2
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    • note
    • 2O, were also examined, but the diazo compound 3a decomposes to give a complex mixture of products.
  • 54
    • 9244265805 scopus 로고    scopus 로고
    • note
    • 1H NMR (400 MHz) spectrum of the crude product of each reaction.
  • 56
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    • unpublished results
    • b) the assignment of the relative stereochemistry is based on the correlation of the product 11a with the known compound (2A,3S)-11a, and an X-ray crystal structure of the reduction product of the racemic α-keto β-amino ester: Y. Zhao, N. Jiang, S. Zhang, J. Wang, unpublished results.
    • Zhao, Y.1    Jiang, N.2    Zhang, S.3    Wang, J.4
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.