Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO.
Org Lett. 2008 Mar 20; 10(6):1043-6.OL

Abstract

Novel bis(thio)urea organocatalysts were synthesized from axially chiral (R)-(-)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (H8-BINAM), and their catalytic abilities have been examined in the Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one or 2-cyclopenten-1-one with a wide range of aromatic aldehydes in combination with DABCO. The best result was achieved in the reaction of 3-fluorobenzaldehyde with 2-cyclohexen-1-one to give the desired Morita-Baylis-Hillman product in 79% yield and 88% ee.

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Authors+Show Affiliations

Shi M

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China. Mshi@mail.sioc.ac.cn

Liu XG

No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18284244

Citation

Shi, Min, and Xu-Guang Liu. "Asymmetric Morita-Baylis-Hillman Reaction of Arylaldehydes With 2-cyclohexen-1-one Catalyzed By Chiral Bis(thio)urea and DABCO." Organic Letters, vol. 10, no. 6, 2008, pp. 1043-6.

Shi M, Liu XG. Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO. Org Lett. 2008;10(6):1043-6.

Shi, M., & Liu, X. G. (2008). Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO. Organic Letters, 10(6), 1043-6. https://doi.org/10.1021/ol7028806

Shi M, Liu XG. Asymmetric Morita-Baylis-Hillman Reaction of Arylaldehydes With 2-cyclohexen-1-one Catalyzed By Chiral Bis(thio)urea and DABCO. Org Lett. 2008 Mar 20;10(6):1043-6. PubMed PMID: 18284244.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO. AU - Shi,Min, AU - Liu,Xu-Guang, Y1 - 2008/02/20/ PY - 2008/2/21/pubmed PY - 2008/2/21/medline PY - 2008/2/21/entrez SP - 1043 EP - 6 JF - Organic letters JO - Org Lett VL - 10 IS - 6 N2 - Novel bis(thio)urea organocatalysts were synthesized from axially chiral (R)-(-)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (H8-BINAM), and their catalytic abilities have been examined in the Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one or 2-cyclopenten-1-one with a wide range of aromatic aldehydes in combination with DABCO. The best result was achieved in the reaction of 3-fluorobenzaldehyde with 2-cyclohexen-1-one to give the desired Morita-Baylis-Hillman product in 79% yield and 88% ee. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18284244/Asymmetric_Morita_Baylis_Hillman_reaction_of_arylaldehydes_with_2_cyclohexen_1_one_catalyzed_by_chiral_bis_thio_urea_and_DABCO_ DB - PRIME DP - Unbound Medicine ER -

Tags

Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO.Org Lett. 2008 Mar 20; 10(6):1043-6.OL