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Volumn 63, Issue 46, 2007, Pages 11307-11314

Facile evolution of asymmetric organocatalysts in water assisted by surfactant Brønsted acids

Author keywords

Aldol; Chiral amine; Michael addition; Surfactant Br nsted acids

Indexed keywords

BRONSTED ACID; DODECYLBENZENESULFONIC ACID; KETONE DERIVATIVE; SURFACTANT; WATER;

EID: 34848919493     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.08.096     Document Type: Article
Times cited : (78)

References (64)
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    • a=9.17. The variation of activity in different media may be rationalized by the following equilibrium, where only species I is catalytically active. (The protonation of pyrrolidinyl nitrogen in a l-prolinamide with strong acids such as p-toluenesulfonic acid leads to an inert catalyst, see:
    • a=9.17. The variation of activity in different media may be rationalized by the following equilibrium, where only species I is catalytically active. (The protonation of pyrrolidinyl nitrogen in a l-prolinamide with strong acids such as p-toluenesulfonic acid leads to an inert catalyst, see:
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    • a of 3-aminopyridine, whereas the use of PB buffer (pH=7.2) helps to shift the equilibrium to I, thus higher activity was achieved in this media.
    • a of 3-aminopyridine, whereas the use of PB buffer (pH=7.2) helps to shift the equilibrium to I, thus higher activity was achieved in this media.
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    • It is known that 2-aminopyridine is a good molecular recognition unit for acids. It is therefore likely the complex of DBSA and catalyst 8 will geometrically facilitate protonation of pyrrolidinyl ring, resulting in exclusively formation of species II (Ref. 14), as a result totally depleting the catalytic activity of catalyst 8. For pyrrolidinyl pyridines as organocatalysts in the absence of acidic additives, see:
    • It is known that 2-aminopyridine is a good molecular recognition unit for acids. It is therefore likely the complex of DBSA and catalyst 8 will geometrically facilitate protonation of pyrrolidinyl ring, resulting in exclusively formation of species II (Ref. 14), as a result totally depleting the catalytic activity of catalyst 8. For pyrrolidinyl pyridines as organocatalysts in the absence of acidic additives, see:. Tang Z., Cun L.-F., Cui X., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. Org. Lett. 8 (2006) 1263-1266
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    • For a few of examples, see:
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    • During the work of this manuscript, Gong reported another example similar with ours, however, the reactions were carried out in organic solvent under lower (-40 °C) temperature, see:
    • Liu Q., and Rovis T. J. Am. Chem. Soc. 128 (2006) 2552-2553 During the work of this manuscript, Gong reported another example similar with ours, however, the reactions were carried out in organic solvent under lower (-40 °C) temperature, see:
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    • note
    • 2=0.0824 (all data).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.