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Volumn 131, Issue 51, 2009, Pages 18244-18245

Direct catalytic asymmetric aldol reactions of thioamides: Toward a stereocontrolled synthesis of 1,3-polyols

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; ALIPHATIC ALDEHYDES; ASYMMETRIC ALDOL REACTIONS; CHEMICAL EQUATIONS; CHEMOSELECTIVE; COOPERATIVE CATALYTIC SYSTEMS; DIRECT ALDOL REACTION; FACILE REDUCTION; POLYOLS; SELF-CONDENSATION; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE MANNER; THIOAMIDES;

EID: 73249116580     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja909758e     Document Type: Article
Times cited : (101)

References (36)
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    • Selected recent examples of the stereoselective synthesis of 1,3-polyols via catalytic asymmetric C-C bond formation: (a) Chandrasekhar, S.; Narsihmulu, C.; Sultana, S. S.; Reddy, M. S. Tetrahedron Lett. 2004, 45, 9299.
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    • General reviews of asymmetric aldol reactions: (a) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
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    • Reviews of direct aldol reactions: a
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    • There are numerous examples of direct aldol reactions using aldol donors bearing electron-withdrawing α-substituents that are readily enolized under mild basic conditions
    • There are numerous examples of direct aldol reactions using aldol donors bearing electron-withdrawing α-substituents that are readily enolized under mild basic conditions.
  • 20
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    • Direct catalytic asymmetric aldol(-type) reactions using aldol donors in the carboxylic acid oxidation state without electron-withdrawing α-substituents: Alkylnitriles: (a) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757. Activated amides:
    • Direct catalytic asymmetric aldol(-type) reactions using aldol donors in the carboxylic acid oxidation state without electron-withdrawing α-substituents: Alkylnitriles: (a) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757. Activated amides:
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    • β,γ-Unsaturated esters
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    • (2006) J. Am. Chem. Soc , vol.128 , pp. 8704
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  • 23
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    • Direct catalytic asymmetric aldol reaction of thiazolidinethiones in which the use of a stoichiometric amount of silylating reagent was essential: Evans, D. A, Downey, C. W, Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706
    • Direct catalytic asymmetric aldol reaction of thiazolidinethiones in which the use of a stoichiometric amount of silylating reagent was essential: Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706.
  • 24
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    • The cross-aldol reaction of aldehydes via asymmetric organocatalysis provides a useful methodology for the synthesis of polyols and sugars. Selected examples: (a) Northrup, A. B, MacMillan, D. W. C. Science 2004, 305, 1752
    • The cross-aldol reaction of aldehydes via asymmetric organocatalysis provides a useful methodology for the synthesis of polyols and sugars. Selected examples: (a) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752.
  • 26
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    • Markert, M, Scheffler, U, Mahrwald, R. J. Am. Chem. Soc. 2009, 131, 16642. Also see ref 6bd. For the relevant catalytic asymmetric C2 elongation using acetaldehyde as the nucleophile, see
    • Markert, M.; Scheffler, U.; Mahrwald, R. J. Am. Chem. Soc. 2009, 131, 16642. Also see ref 6bd. For the relevant catalytic asymmetric C2 elongation using acetaldehyde as the nucleophile, see:
  • 29
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    • Asymmetric aldol reaction of thioamides with a stoichiometric chiral source: (a) Cinquini, M.; Manfredi, A.; Molinari, H.; Restelli, A. Tetrahedron 1985, 41, 4929.
    • Asymmetric aldol reaction of thioamides with a stoichiometric chiral source: (a) Cinquini, M.; Manfredi, A.; Molinari, H.; Restelli, A. Tetrahedron 1985, 41, 4929.
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    • See the Supporting Information
    • See the Supporting Information.
  • 33
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    • Aromatic aldehydes were more reactive in this system, leading to retroaldol reaction and dehydration of the aldol product (e.g., benzaldehyde: 66% yield, 72% ee). Further investigations are currently underway.
    • Aromatic aldehydes were more reactive in this system, leading to retroaldol reaction and dehydration of the aldol product (e.g., benzaldehyde: 66% yield, 72% ee). Further investigations are currently underway.
  • 35
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    • Recent selected examples of catalyst-controlled diastereoselectivity: (a) Balskus, E. P.; Jacobsen, E. N. Science 2007, 317, 1736.
    • Recent selected examples of catalyst-controlled diastereoselectivity: (a) Balskus, E. P.; Jacobsen, E. N. Science 2007, 317, 1736.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.