A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction
نویسندگان
چکیده
منابع مشابه
A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction.
A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.
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Remarkable generality in scope of DATs/Cu catalysts for enantioselective nitroaldol reaction is described; excellent levels of stereoinduction are recorded for a range of aldehydes (ee 81-99%, 17 examples) and the possibility to employ the present catalytic system as the key step for the preparation of highly functionalized tetrahydro-isoquinolines is demonstrated.
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A C(2)-symmetric diethyl (i)Pr-bis(oxazoline)-Cu(OAc)(2).H(2)O was found to be an efficient catalyst for catalyzing an enantioselective Henry reaction between nitromethane and various aldehydes to provide beta-hydroxy nitroalkanes with high chemical yields (up to 95%) and enantiomeric excesses (up to 97%).
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Remarkable generality in scope of new C9-benzoylcupreines bearing electron-withdrawing substituents for the nitroaldol condensation with fluoromethyl ketones is presented. Both tri- and difluoromethyl ketones provided excellent levels of stereoinduction (ee 76-99%) under mild reaction conditions and low loading of catalyst (1-5 mol%).
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The C-C bond formation is an important reaction in organic synthesis to obtain value-added intermediates. Therefore, in this paper an attempt has been made to accelerate the Henry reaction (C-C bond formation) between aryl aldehydes and nitromethane using less expensive whole cell biocatalyst, baker’s yeast (BY). The scope of the methodology was also tested for the heteryl aldehyde i.e. 2-chlor...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2003
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja0373871