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Volumn , Issue 9, 2010, Pages 1717-1727

Ketopinic acid derived bis(hydroxy amides) as cheap, chiral ligands for the enantioselective ethylation of aromatic aldehydes

Author keywords

Asymmetric catalysis; Chiral pool; Hydroxy amides; Structure activity relationships; Zinc

Indexed keywords


EID: 77949300467     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901391     Document Type: Article
Times cited : (10)

References (67)
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    • Patent No. US 5977371
    • [1g] for some additional, interesting examples. On liquid-crystal preparation, see: d) J. D. Armstrong, J. C. McWilliams, Patent No. US 5977371;
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    • some recent examples of the synthesis of useful, chiral, building blocks are: e) K. Yeanick, C. Wolf, Org. Lett. 2008, 10, 3015-3918;
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    • SciFinder (copyright 2009 CAS; licensed to UCM) finds ca. 1500 references by crossing the topics "diethylzinc" and "enantioselective" .
    • SciFinder (copyright 2009, CAS; licensed to UCM) finds ca. 1500 references by crossing the topics "diethylzinc" and "enantioselective".
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    • nevertheless, from a functional point of view, the involved ligand must be considered a hydroxy-imine-based ligand.
    • A third example describing an efficient chiral imino-hydroxyamide (93% ee in the aldehyde ethylation) was previously reported: A. Mori, D. Yu, S. Inoue, Synlett 1992, 427-428; nevertheless, from a functional point of view, the involved ligand must be considered a hydroxy-imine-based ligand.
    • (1992) Synlett , pp. 427-428
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    • A. cheaper amidation of ketopmic acid can be achieved by acidic activation with thionyl chloride (ketopinoyl chloride generation). For example, see ref.[18,20a,21]
    • A. cheaper amidation of ketopmic acid can be achieved by acidic activation with thionyl chloride (ketopinoyl chloride generation). For example, see ref.[18,20a,21]
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    • 4 for the stereoselective reduction of 16g and 16h (see ref.[21])
    • 4 for the stereoselective reduction of 16g and 16h (see ref.[21]).
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    • 2-symmetric catalysts from ketopinic acid derived, protic-amide-based bis(hydroxy amides) with short diamine spacers (e.g., see the use of ligands 14g-h in ref.[21]).
    • 2-symmetric catalysts from ketopinic acid derived, protic-amide-based bis(hydroxy amides) with short diamine spacers (e.g., see the use of ligands 14g-h in ref.[21]).
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    • Note that the formation of an N-coordinated, zinc-centered complex (-CO-N-Zn-N-CO-) from a 2-carbon-spacer bis(hydroxy amide) should involve a rigid five-membered-ring spacer, whereas the carbonyl-chelated one (-N-C=O-Zn-O=C-N-) involves a less rigid, eight-membered-ring spacer.
    • Note that the formation of an N-coordinated, zinc-centered complex (-CO-N-Zn-N-CO-) from a 2-carbon-spacer bis(hydroxy amide) should involve a rigid five-membered-ring spacer, whereas the carbonyl-chelated one (-N-C=O-Zn-O=C-N-) involves a less rigid, eight-membered-ring spacer.
  • 66
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    • The reduction of the ligand loading results in the different behavior of these diastereomeric ligands (see Table 4).
    • The reduction of the ligand loading results in the different behavior of these diastereomeric ligands (see Table 4).
  • 67
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    • Walsh has demonstrated the utility of highly concentrated conditions for enantioselective ketone alkylations: S.-J. Jeon, H. Li, P. J. Walsh, J. Am. Chem. Soc, 2005, 127, 16416-16425.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 16416-16425
    • Jeon, S.-J.1    Li, H.2    Walsh, P.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.