Tags

Type your tag names separated by a space and hit enter

Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: challenging leaving groups.
Org Lett. 2014 Mar 21; 16(6):1570-3.OL

Abstract

C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Huo X
School of Pharmacy and ‡School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, P. R. China.
Quan M
No affiliation info available
Yang G
No affiliation info available
Zhao X
No affiliation info available
Liu D
No affiliation info available
Liu Y
No affiliation info available
Zhang W
No affiliation info available

MeSH

AlcoholsAlkylationAllyl CompoundsCatalysisCombinatorial Chemistry TechniquesEthersHydrogen BondingMolecular StructurePalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24621181

Citation

Huo, Xiaohong, et al. "Hydrogen-bond-activated Palladium-catalyzed Allylic Alkylation Via Allylic Alkyl Ethers: Challenging Leaving Groups." Organic Letters, vol. 16, no. 6, 2014, pp. 1570-3.
Huo X, Quan M, Yang G, et al. Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: challenging leaving groups. Org Lett. 2014;16(6):1570-3.
Huo, X., Quan, M., Yang, G., Zhao, X., Liu, D., Liu, Y., & Zhang, W. (2014). Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: challenging leaving groups. Organic Letters, 16(6), 1570-3. https://doi.org/10.1021/ol5000988
Huo X, et al. Hydrogen-bond-activated Palladium-catalyzed Allylic Alkylation Via Allylic Alkyl Ethers: Challenging Leaving Groups. Org Lett. 2014 Mar 21;16(6):1570-3. PubMed PMID: 24621181.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: challenging leaving groups. AU - Huo,Xiaohong, AU - Quan,Mao, AU - Yang,Guoqiang, AU - Zhao,Xiaohu, AU - Liu,Delong, AU - Liu,Yangang, AU - Zhang,Wanbin, Y1 - 2014/03/12/ PY - 2014/3/14/entrez PY - 2014/3/14/pubmed PY - 2014/6/4/medline SP - 1570 EP - 3 JF - Organic letters JO - Org Lett VL - 16 IS - 6 N2 - C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24621181/Hydrogen_bond_activated_palladium_catalyzed_allylic_alkylation_via_allylic_alkyl_ethers:_challenging_leaving_groups_ DB - PRIME DP - Unbound Medicine ER -