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An enantioselective organocatalyzed aza-Morita-Baylis-Hillman reaction of isatin-derived ketimines with acrolein.
Org Biomol Chem. 2015 Sep 14; 13(34):9022-8.OB

Abstract

A highly enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with acrolein was established using β-isocupreidine (β-ICD) or α-isocupreine (α-ICPN) as a chiral acid-base organocatalyst. The present protocol readily furnished (S) or (R)-aza-MBH adducts with a chiral tetrasubstituted carbon stereogenic center in up to 98% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yoshida Y
The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
Sako M
No affiliation info available
Kishi K
No affiliation info available
Sasai H
No affiliation info available
Hatakeyama S
No affiliation info available
Takizawa S
No affiliation info available

MeSH

AcroleinCatalysisHydroxyquinolinesIminesIsatinMolecular StructureNitrilesQuinuclidinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

26214279

Citation

Yoshida, Yasushi, et al. "An Enantioselective Organocatalyzed aza-Morita-Baylis-Hillman Reaction of Isatin-derived Ketimines With Acrolein." Organic & Biomolecular Chemistry, vol. 13, no. 34, 2015, pp. 9022-8.
Yoshida Y, Sako M, Kishi K, et al. An enantioselective organocatalyzed aza-Morita-Baylis-Hillman reaction of isatin-derived ketimines with acrolein. Org Biomol Chem. 2015;13(34):9022-8.
Yoshida, Y., Sako, M., Kishi, K., Sasai, H., Hatakeyama, S., & Takizawa, S. (2015). An enantioselective organocatalyzed aza-Morita-Baylis-Hillman reaction of isatin-derived ketimines with acrolein. Organic & Biomolecular Chemistry, 13(34), 9022-8. https://doi.org/10.1039/c5ob00874c
Yoshida Y, et al. An Enantioselective Organocatalyzed aza-Morita-Baylis-Hillman Reaction of Isatin-derived Ketimines With Acrolein. Org Biomol Chem. 2015 Sep 14;13(34):9022-8. PubMed PMID: 26214279.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An enantioselective organocatalyzed aza-Morita-Baylis-Hillman reaction of isatin-derived ketimines with acrolein. AU - Yoshida,Yasushi, AU - Sako,Makoto, AU - Kishi,Kenta, AU - Sasai,Hiroaki, AU - Hatakeyama,Susumi, AU - Takizawa,Shinobu, Y1 - 2015/07/27/ PY - 2015/7/28/entrez PY - 2015/7/28/pubmed PY - 2016/5/18/medline SP - 9022 EP - 8 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 13 IS - 34 N2 - A highly enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with acrolein was established using β-isocupreidine (β-ICD) or α-isocupreine (α-ICPN) as a chiral acid-base organocatalyst. The present protocol readily furnished (S) or (R)-aza-MBH adducts with a chiral tetrasubstituted carbon stereogenic center in up to 98% ee. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/26214279/An_enantioselective_organocatalyzed_aza_Morita_Baylis_Hillman_reaction_of_isatin_derived_ketimines_with_acrolein_ DB - PRIME DP - Unbound Medicine ER -