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A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction.
J Am Chem Soc. 2003 Oct 22; 125(42):12692-3.JA

Abstract

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.

Authors+Show Affiliations

Evans DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Seidel D
No affiliation info available
Rueping M
No affiliation info available
Lam HW
No affiliation info available
Shaw JT
No affiliation info available
Downey CW
No affiliation info available

MeSH

AcetatesAlcoholsCatalysisCopperMethaneNitro CompoundsNitroparaffinsOrganometallic CompoundsOxazolesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

14558801

Citation

Evans, David A., et al. "A New Copper Acetate-bis(oxazoline)-catalyzed, Enantioselective Henry Reaction." Journal of the American Chemical Society, vol. 125, no. 42, 2003, pp. 12692-3.
Evans DA, Seidel D, Rueping M, et al. A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction. J Am Chem Soc. 2003;125(42):12692-3.
Evans, D. A., Seidel, D., Rueping, M., Lam, H. W., Shaw, J. T., & Downey, C. W. (2003). A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction. Journal of the American Chemical Society, 125(42), 12692-3.
Evans DA, et al. A New Copper Acetate-bis(oxazoline)-catalyzed, Enantioselective Henry Reaction. J Am Chem Soc. 2003 Oct 22;125(42):12692-3. PubMed PMID: 14558801.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction. AU - Evans,David A, AU - Seidel,Daniel, AU - Rueping,Magnus, AU - Lam,Hon Wai, AU - Shaw,Jared T, AU - Downey,C Wade, PY - 2003/10/16/pubmed PY - 2003/12/18/medline PY - 2003/10/16/entrez SP - 12692 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 42 N2 - 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. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/14558801/A_new_copper_acetate_bis_oxazoline__catalyzed_enantioselective_Henry_reaction_ DB - PRIME DP - Unbound Medicine ER -