A highly efficient Mukaiyama-Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf.
Org Biomol Chem. 2015 Dec 07; 13(45):10968-72.OB

Abstract

Ph3PAuOTf is identified as a powerful catalyst for the addition of difluoroenol silyl ethers to N-Boc isatin ketimines and other two kinds of active cyclic ketimines. This represents the first Au(i)-catalyzed Mukaiyama-Mannich reaction, and the corresponding non-fluorinated enol silyl ether proves to be even much more reactive under the same conditions. This method paves the way to the total synthesis of difluoromethylated analogues of AG-041R, a gastrin/CCK-B receptor antagonist.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Yu JS

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062, China. jzhou@chem.ecnu.edu.cn.

Zhou J

No affiliation info available

MeSH

CatalysisCyclizationEthersGoldHalogenationIminesIndolesIsatinMannich BasesMethylationNitriles

Pub Type(s)

Journal Article

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

Language

eng

PubMed ID

26443467

Citation

Yu, Jin-Sheng, and Jian Zhou. "A Highly Efficient Mukaiyama-Mannich Reaction of N-Boc Isatin Ketimines and Other Active Cyclic Ketimines Using Difluoroenol Silyl Ethers Catalyzed By Ph3PAuOTf." Organic & Biomolecular Chemistry, vol. 13, no. 45, 2015, pp. 10968-72.

Yu JS, Zhou J. A highly efficient Mukaiyama-Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf. Org Biomol Chem. 2015;13(45):10968-72.

Yu, J. S., & Zhou, J. (2015). A highly efficient Mukaiyama-Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf. Organic & Biomolecular Chemistry, 13(45), 10968-72. https://doi.org/10.1039/c5ob01895a

Yu JS, Zhou J. A Highly Efficient Mukaiyama-Mannich Reaction of N-Boc Isatin Ketimines and Other Active Cyclic Ketimines Using Difluoroenol Silyl Ethers Catalyzed By Ph3PAuOTf. Org Biomol Chem. 2015 Dec 7;13(45):10968-72. PubMed PMID: 26443467.

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

TY - JOUR T1 - A highly efficient Mukaiyama-Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf. AU - Yu,Jin-Sheng, AU - Zhou,Jian, Y1 - 2015/10/07/ PY - 2015/10/8/entrez PY - 2015/10/8/pubmed PY - 2016/6/9/medline SP - 10968 EP - 72 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 13 IS - 45 N2 - Ph3PAuOTf is identified as a powerful catalyst for the addition of difluoroenol silyl ethers to N-Boc isatin ketimines and other two kinds of active cyclic ketimines. This represents the first Au(i)-catalyzed Mukaiyama-Mannich reaction, and the corresponding non-fluorinated enol silyl ether proves to be even much more reactive under the same conditions. This method paves the way to the total synthesis of difluoromethylated analogues of AG-041R, a gastrin/CCK-B receptor antagonist. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/26443467/A_highly_efficient_Mukaiyama_Mannich_reaction_of_N_Boc_isatin_ketimines_and_other_active_cyclic_ketimines_using_difluoroenol_silyl_ethers_catalyzed_by_Ph3PAuOTf_ DB - PRIME DP - Unbound Medicine ER -

Tags

A highly efficient Mukaiyama-Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf.Org Biomol Chem. 2015 Dec 07; 13(45):10968-72.OB