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Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex.
J Am Chem Soc. 2009 Oct 28; 131(42):15118-9.JA

Abstract

An aluminum complex was found to be high yielding and enantioselective for the addition of cyanide to aldimines and ketimines. Although catalytic asymmetric addition of cyanide to imines to generate alpha-amino-protected nitriles (the Strecker reaction) has been extensively studied in the past, alternative, easier-to-handle reagents for this process are required for modern organic synthesis. To date, there are a limited number of reports utilizing alternative sources of cyanide other than KCN/HCN or TMSCN for this important reaction. The present catalyst provides uniformly high enantioselectivity for aromatic, heteroaromatic, and aliphatic aldimines and ketimines using ethyl cyanoformate as the cyanide source.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Abell JP
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Yamamoto H
No affiliation info available

MeSH

CatalysisCyanidesIminesMolecular StructureOrganometallic CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19799383

Citation

Abell, Joshua P., and Hisashi Yamamoto. "Dual-activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed By a Tethered Bis(8-quinolinolato) Aluminum Complex." Journal of the American Chemical Society, vol. 131, no. 42, 2009, pp. 15118-9.
Abell JP, Yamamoto H. Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex. J Am Chem Soc. 2009;131(42):15118-9.
Abell, J. P., & Yamamoto, H. (2009). Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex. Journal of the American Chemical Society, 131(42), 15118-9. https://doi.org/10.1021/ja907268g
Abell JP, Yamamoto H. Dual-activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed By a Tethered Bis(8-quinolinolato) Aluminum Complex. J Am Chem Soc. 2009 Oct 28;131(42):15118-9. PubMed PMID: 19799383.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex. AU - Abell,Joshua P, AU - Yamamoto,Hisashi, PY - 2009/10/6/entrez PY - 2009/10/6/pubmed PY - 2010/2/19/medline SP - 15118 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 131 IS - 42 N2 - An aluminum complex was found to be high yielding and enantioselective for the addition of cyanide to aldimines and ketimines. Although catalytic asymmetric addition of cyanide to imines to generate alpha-amino-protected nitriles (the Strecker reaction) has been extensively studied in the past, alternative, easier-to-handle reagents for this process are required for modern organic synthesis. To date, there are a limited number of reports utilizing alternative sources of cyanide other than KCN/HCN or TMSCN for this important reaction. The present catalyst provides uniformly high enantioselectivity for aromatic, heteroaromatic, and aliphatic aldimines and ketimines using ethyl cyanoformate as the cyanide source. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/19799383/Dual_activation_asymmetric_strecker_reaction_of_aldimines_and_ketimines_catalyzed_by_a_tethered_bis_8_quinolinolato__aluminum_complex_ L2 - https://doi.org/10.1021/ja907268g DB - PRIME DP - Unbound Medicine ER -