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Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones.
Org Biomol Chem. 2015 Nov 21; 13(43):10691-8.OB

Abstract

An enantioselective conjugate addition of boron to α,β-unsaturated ketones catalysed by either a N-heterocyclic carbene or a copper-carbene complex generated in situ from a new chiral bicyclic triazolium based on [2.2]paracyclophane is presented. The dual chiral carbene-copper catalyst has significant advantages over its carbene counterpart as an organocatalyst in asymmetric β-boration of acyclic enones, giving a variety of chiral β-boryl ketones in good yields and enantioselectivities. This is a successful example of employing the same N-heterocyclic carbene in one catalytic reaction as both an organocatalyst and a ligand for transition metal catalysis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang L
Department of Chemistry, Shandong University, Shanda South Road No. 27, Jinan 250100, China. ydma@sdu.edu.cn.
Chen Z
Department of Chemistry, Shandong University, Shanda South Road No. 27, Jinan 250100, China. ydma@sdu.edu.cn.
Ma M
School of Pharmaceutical Sciences, West Wenhua Road No. 44, Jinan 250012, China. chunsong@sdu.edu.cn.
Duan W
School of Chemistry and Chemical Engineering, Liaocheng University, Hunan Road No. 1, Liaocheng 252000, China.
Song C
School of Pharmaceutical Sciences, West Wenhua Road No. 44, Jinan 250012, China. chunsong@sdu.edu.cn.
Ma Y
Department of Chemistry, Shandong University, Shanda South Road No. 27, Jinan 250100, China. ydma@sdu.edu.cn.

MeSH

BoronBoron CompoundsCatalysisCopperHeterocyclic CompoundsKetonesMethanePolycyclic CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

26347490

Citation

Wang, Lei, et al. "Synthesis and Application of a Dual Chiral [2.2]paracyclophane-based N-heterocyclic Carbene in Enantioselective Β-boration of Acyclic Enones." Organic & Biomolecular Chemistry, vol. 13, no. 43, 2015, pp. 10691-8.
Wang L, Chen Z, Ma M, et al. Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones. Org Biomol Chem. 2015;13(43):10691-8.
Wang, L., Chen, Z., Ma, M., Duan, W., Song, C., & Ma, Y. (2015). Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones. Organic & Biomolecular Chemistry, 13(43), 10691-8. https://doi.org/10.1039/c5ob01609f
Wang L, et al. Synthesis and Application of a Dual Chiral [2.2]paracyclophane-based N-heterocyclic Carbene in Enantioselective Β-boration of Acyclic Enones. Org Biomol Chem. 2015 Nov 21;13(43):10691-8. PubMed PMID: 26347490.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones. AU - Wang,Lei, AU - Chen,Zhen, AU - Ma,Manyuan, AU - Duan,Wenzeng, AU - Song,Chun, AU - Ma,Yudao, PY - 2015/9/9/entrez PY - 2015/9/9/pubmed PY - 2016/7/28/medline SP - 10691 EP - 8 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 13 IS - 43 N2 - An enantioselective conjugate addition of boron to α,β-unsaturated ketones catalysed by either a N-heterocyclic carbene or a copper-carbene complex generated in situ from a new chiral bicyclic triazolium based on [2.2]paracyclophane is presented. The dual chiral carbene-copper catalyst has significant advantages over its carbene counterpart as an organocatalyst in asymmetric β-boration of acyclic enones, giving a variety of chiral β-boryl ketones in good yields and enantioselectivities. This is a successful example of employing the same N-heterocyclic carbene in one catalytic reaction as both an organocatalyst and a ligand for transition metal catalysis. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/26347490/Synthesis_and_application_of_a_dual_chiral_[2_2]paracyclophane_based_N_heterocyclic_carbene_in_enantioselective_β_boration_of_acyclic_enones_ DB - PRIME DP - Unbound Medicine ER -