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Volumn 10, Issue 16, 2008, Pages 3521-3524

Diastereodivergent Aldol reactions of β-alkoxy ethyl ketones: Modular access to (1,4)-syn and -anti polypropionates

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; KETONE; POLYMER; PROPIONIC ACID DERIVATIVE;

EID: 54049086638     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801292t     Document Type: Article
Times cited : (29)

References (48)
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    • For recent reviews, see: a
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    • According to the (1,n)-nomenclature, 1 denotes the newly formed stereogenic center, while n stands for the pre-existing chiral center.
    • According to the (1,n)-nomenclature, 1 denotes the newly formed stereogenic center, while n stands for the pre-existing chiral center.
  • 9
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    • For a leading reference on substrate-controlled aldol reactions of enolates bearing different substitution patterns as compared to the one discussed herein, see ref 4b and Braun, M. In Modern Aldol Reactions; Mahrwald, R, Ed, Wiley-VCH: Weinheim, 2004; pp 1-61
    • For a leading reference on substrate-controlled aldol reactions of enolates bearing different substitution patterns as compared to the one discussed herein, see ref 4b and Braun, M. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; pp 1-61.
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    • For selected references of aldol additions with substrate control of ethyl ketones which are structurally related to 4, see: (a) McCarthy, P, Kageyama, M. J. Org. Chem. 1987, 52, 4681
    • For selected references of aldol additions with substrate control of ethyl ketones which are structurally related to 4, see: (a) McCarthy, P.; Kageyama, M. J. Org. Chem. 1987, 52, 4681.
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    • For selected reference of aldol additions with substrate control from chiral methyl ketones, which are structurally related to 4, see: (a) Evans, D. A.; Gage, J. R. Tetrahedron Lett. 1990, 31, 6129.
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    • (1997) Org. React , vol.51 , pp. 1
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    • For leading references on the stereochemical influence of the α-and β-chiral center of the aldehyde in aldol reactions, see: (a) Roush, W. R. J. Org. Chem. 1991, 56, 4151.
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    • For recent examples of diversity-oriented polyketide library synthesis, see: a
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    • In 1,5-anti aldol reactions of certain β-alkyxyketones, the β-substituent appears to be more influential as compared to the α-substituent; see ref 8f and literature cited therein
    • In 1,5-anti aldol reactions of certain β-alkyxyketones, the β-substituent appears to be more influential as compared to the α-substituent; see ref 8f and literature cited therein.
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    • Selection of 3 and 4 was based on preliminary studies on the configurational assignment of etnangien in our own laboratories.
    • Selection of 3 and 4 was based on preliminary studies on the configurational assignment of etnangien in our own laboratories.
  • 37
    • 61349110558 scopus 로고    scopus 로고
    • This noncyclic transition state is in agreement with that proposed by Evans for a boron-mediated aldol reaction.14c For titanium-mediated aldol couplings, a different noncyclic model has been discussed.7b
    • 7b
  • 39
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    • Mukayiama-type aldol reactions were not evaluated within this study because of practicality, as they require separate silyl-enol-ether formation
    • Mukayiama-type aldol reactions were not evaluated within this study because of practicality, as they require separate silyl-enol-ether formation.
  • 40
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    • Analogous boron9 and titanium7b gave lower π-face selectivity and/ or proceeded with lower yields
    • 7b gave lower π-face selectivity and/ or proceeded with lower yields.
  • 41
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    • Tin enolates were first introduced by Mukaiyama: Mukaiyama, T.; Iwasawa, N.; Stevens, R. W.; Haga, T. Tetrahedron 1984, 40, 1381.
    • Tin enolates were first introduced by Mukaiyama: Mukaiyama, T.; Iwasawa, N.; Stevens, R. W.; Haga, T. Tetrahedron 1984, 40, 1381.
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    • In all cases, dr refers to the diastereomeric ratio of the 1,4-syn to the 1,4-anti aldol products
    • In all cases, dr refers to the diastereomeric ratio of the 1,4-syn to the 1,4-anti aldol products.
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    • For a leading reference on titanium-mediated aldol reactions, see:, Mahrwald, R, Ed, Wiley-VCH: Weinheim
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    • For good stereoselectivities, short reaction times were beneficial. 7c
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.