A series of dipeptide analogues consisting of proline, phenylalanine and aniline- or phenol-fluorine derivatives were synthesized. Their catalytic ability was evaluated in the intermolecular asymmetric aldol reaction, both in organic and aqueous media. Aniline-fluorine derivatives proved to be superior and the best results were obtained, when 2-CF3 aniline was employed. A diverse substrate scope consisting of both aromatic and aliphatic aldehydes, as well as different ketones was demonstrated, where aromatic aldehydes afforded products in high yields (up to 100%) with excellent diastereo- (up to 95:5) and enantioselectivities (up to 97%), whereas the aliphatic aldehydes afforded also excellent selectivities, but relatively low yield. A simple addition of fluorine to a dipeptide analogue affords organocatalysts with new interesting properties that can catalyze the aldol reaction more efficiently. (C) 2018 Elsevier Ltd. All rights reserved.
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Univ York, Dept Chem, York YO10 5DD, North Yorks, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Clarke, Paul A.
Forintos, Henrietta
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Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Forintos, Henrietta
Gilks, James A. R.
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Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Gilks, James A. R.
Hayes, Christopher J.
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Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Hayes, Christopher J.
Vale, Matthew E.
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Univ York, Dept Chem, York YO10 5DD, North Yorks, England
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Vale, Matthew E.
Wade, William
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Univ York, Dept Chem, York YO10 5DD, North Yorks, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Wade, William
Zbytniewski, Myriam
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Univ York, Dept Chem, York YO10 5DD, North Yorks, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
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Yale Univ, Dept Chem, New Haven, CT 06520 USA
Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USA
Assumption Coll, Worcester, MA 01609 USAYale Univ, Dept Chem, New Haven, CT 06520 USA
Davie, Elizabeth A. Colby
Mennen, Steven M.
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Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USAYale Univ, Dept Chem, New Haven, CT 06520 USA
Mennen, Steven M.
Xu, Yingju
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Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USAYale Univ, Dept Chem, New Haven, CT 06520 USA
Xu, Yingju
Miller, Scott J.
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Yale Univ, Dept Chem, New Haven, CT 06520 USA
Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USAYale Univ, Dept Chem, New Haven, CT 06520 USA
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Univ York, Dept Chem, York YO10 5DD, North Yorks, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Clarke, Paul A.
Forintos, Henrietta
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h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Forintos, Henrietta
Gilks, James A. R.
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h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Gilks, James A. R.
Hayes, Christopher J.
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h-index: 0
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Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Hayes, Christopher J.
Vale, Matthew E.
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h-index: 0
机构:
Univ York, Dept Chem, York YO10 5DD, North Yorks, England
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Vale, Matthew E.
Wade, William
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h-index: 0
机构:
Univ York, Dept Chem, York YO10 5DD, North Yorks, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
Wade, William
Zbytniewski, Myriam
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h-index: 0
机构:
Univ York, Dept Chem, York YO10 5DD, North Yorks, EnglandUniv York, Dept Chem, York YO10 5DD, North Yorks, England
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USA
Assumption Coll, Worcester, MA 01609 USAYale Univ, Dept Chem, New Haven, CT 06520 USA
Davie, Elizabeth A. Colby
Mennen, Steven M.
论文数: 0引用数: 0
h-index: 0
机构:
Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USAYale Univ, Dept Chem, New Haven, CT 06520 USA
Mennen, Steven M.
Xu, Yingju
论文数: 0引用数: 0
h-index: 0
机构:
Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USAYale Univ, Dept Chem, New Haven, CT 06520 USA
Xu, Yingju
Miller, Scott J.
论文数: 0引用数: 0
h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USAYale Univ, Dept Chem, New Haven, CT 06520 USA