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Volumn 45, Issue 19, 2006, Pages 3146-3150

Trichloromethyl ketones as synthetically versatile donors: Application in direct catalytic mannich-type reactions and the stereoselective synthesis of azetidines

Author keywords

Asymmetric catalysis; Azetidines; Diastereoselectivity; Mannich reaction; Trichloromethyl ketones

Indexed keywords

CARBON; CATALYSIS; CHEMICAL BONDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33746255430     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600227     Document Type: Article
Times cited : (62)

References (68)
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    • For exceptional results with methyl trichloromethylacetoacetate and 4,4,4-trichloromethyl-3-oxobutanal as nucleophiles in Knoevenagel condensations, see: a) L. F. Tietze, H. Meier, H. Nutt, Chem. Ber. 1989, 122, 643;
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    • For recent reports of Favorskii rearrangements and related reactions of acyclic trihalomethyl ketones, including trichloromethyl ketones under basic conditions, see: a) S. Braverman, M. Cherkinsky, E. V. K. S. Kumar, H. E. Gottlieb, Tetrahedron 2000, 56, 4521;
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    • although trichloromethyl carbinols were oxidized mainly by using stoichiometric amounts of chromium(VI) reagents in the original report, we utilized the catalytic oxidation method reported by workers at Merck: b) M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, Tetrahedron Lett. 1998, 39, 5323; Swern oxidation is also applicable, see Supporting Information.
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    • note
    • 2} (10 mol%), also promoted the Mannich reaction of imine 2d with 1a (5 equiv) at -40°C in comparable yield (conv. 89%), albeit with lower syn selectivity (syn/anti = 13:1) and longer reaction time (13h) than the corresponding reactions in Table 1.
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    • The N-Dpp group is useful because it is readily removed; for a review on the use of N-Dpp imines in organic synthesis, see: S. M. Weinreb, R. K. Orr, Synthesis 2005, 1205.
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    • note
    • [22] the relative configurations of 3da and 3la were determined after conversion into known compounds; see Supporting Information.
  • 60
    • 33746235135 scopus 로고    scopus 로고
    • Wiley, New York, chap. 9, see also reference [11c]
    • For discussions on steric effects of the trichloromethyl group, see: M. B. Smith, J. March, Advanced Organic Chemistry, 5th ed., Wiley, New York, 2001, chap. 9, p. 374; see also reference [11c].
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    • note
    • The relative configuration of 8da was determined by X-ray crystallographic analysis of the corresponding cyclic carbamate; see Supporting Information.
  • 62
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    • note
    • For the determination of the relative configurations of 10da and 12da, see Supporting Information.
  • 63
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    • CCDC 295183-295185 (12da, 3fa, cyclic carbamate derived from 8da, respectively) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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    • and references therein
    • For the synthesis of azetidine-2-carboxylic acids (L-aze analogues) and their incorporation into peptides, see the review: a) F. Couty, G. Evano, D. Prim, Mini-Rev. Org. Chem. 2004, 1, 133, and references therein;
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    • for selected recent examples, see: b) D. Enders, J. Gries, Synthesis 2005, 3508, and references therein;
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    • Enders, D.1    Gries, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.