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Volumn 35, Issue 48, 1994, Pages 9083-9086

Studies in polypropionate synthesis: High π-face selectivity in syn and anti aldol reactions of chiral boron enolates of lactate-derived ketones

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

EID: 0028151214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(94)88434-X     Document Type: Article
Times cited : (143)

References (36)
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    • For related Li- and Ti(IV)-mediated, syn aldol reactions, see
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  • 9
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    • α′-Benzoyloxy and α′-methoxymethoxy lithium enolates giving opposite diastereofacial selectivities in aldol reactions. Use of (probable) extended chelation for reversal of stereoselectivities
    • (1993) Tetrahedron Letters , vol.34 , pp. 2221
    • Choudhury1    Thornton2
  • 10
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    • New methods and strategies for the stereocontrolled synthesis of polypropionate-derived natural products
    • (1992) Pure and Applied Chemistry , vol.64 , pp. 1821
    • Paterson1
  • 12
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    • Aldol reactions in polypropionate synthesis: High π-face selectivity of enol borinates from α-chiral methyl and ethyl ketones under substrate control
    • (1989) Tetrahedron Letters , vol.30 , pp. 7121
    • Paterson1    Goodman2    Isaka3
  • 13
    • 0026703867 scopus 로고
    • Studies in polypropionate synthesis: high π-face selectivity in syn aldol reactions of tin(II) enolates from (R)- and (S)-1-benzyloxy-2-methylpentan-3-one.
    • (1992) Tetrahedron Letters , vol.33 , pp. 4233
    • Paterson1    Tillyer2
  • 16
    • 0027183899 scopus 로고
    • High π-face selectivity in anti aldol reactions of E-enol borinates from chiral alkoxymethyl ketones: stereocontrolled synthesis of a C24-C32 polyol subunit of rapamycin
    • (1993) The Journal of Organic Chemistry , vol.58 , pp. 4182
    • Paterson1    Tillyer2
  • 17
    • 0000444632 scopus 로고
    • 1,4-Diastereoselectivity in the aldol condensation of methyl ketones
    • For stereoselective Mukaiyama aldol reactions of lactate-derived methyl ketones, see
    • (1990) The Journal of Organic Chemistry , vol.55 , pp. 3982
    • Trost1    Urabe2
  • 22
    • 0028046376 scopus 로고
    • Manipulation of the aldol adducts from lactate-derived ketones. A versatile chiral auxiliary for the asymmetric synthesis of β-hydroxy carbonyl compounds
    • (following paper)
    • (1994) Tetrahedron Letters , vol.35 , pp. 9087
    • Paterson1    Wallace2
  • 25
    • 84912979347 scopus 로고    scopus 로고
    • All new compounds gave spectroscopic data in agreement with the assigned structures. See ref 7, for proof of aldol stereochemistry.
  • 29
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    • Stereocontrolled, two-directional, chain synthesis using the Boron Aldol reaction and double Ireland-Claisen rearrangement.
    • (1991) Tetrahedron Letters , vol.32 , pp. 7601
    • Paterson1    Hulme2    Wallace3
  • 30
    • 0026553351 scopus 로고
    • Diastereoselective Anti Aldol Reactions of Chiral Ethyl Ketones. Enantioselective Processes for the Synthesis of Polypropionate Natural Products.
    • (1992) Tetrahedron , vol.48 , pp. 2127
    • Evans1    Ng2    Clark3    Rieger4
  • 31
    • 0026487205 scopus 로고
    • Enolisation of ketones by dialkylboron chlorides and trifiates: A model for the effect of reagent leaving group substrate structure and amine base.
    • 3N. With the benzoate 7, chelation is expected to be precluded and normal cis deprotonation giving the E enol borinate now occurs. For a relevant discussion of enolisation stereocontrol, see
    • (1992) Tetrahedron Letters , vol.33 , pp. 7223
    • Goodman1    Paterson2
  • 32
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    • 2O/hexane) and/or flash chromatography to give the major anti aldol adduct 11. A [[Truncated]]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.