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Access to Spiroindolines and Spirodihydrobenzofurans via Pd-Catalyzed Domino Heck Spiroyclization through C-H Activation and Carbene Insertion.
Org Lett. 2018 05 04; 20(9):2728-2732.OL

Abstract

A new palladium-catalyzed domino approach for the synthesis of attractive spirocyclic indolines and dihydrobenzofurans was developed. The reaction proceeds through a sequential intramolecular Heck spirocyclization, remote C-H activation, and diazocarbonyl carbene insertion. Various spiroindolines and spirodihydrobenzofurans containing two quartenary carbon stereocenters were readily obtained in good to excellent yields. A preliminary study of asymmetric spirocyclization using chiral monophosphoramidite as a ligand was also conducted, enabling access to highly valuable chiral spiroindolines with up to 80% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu JG
Department of Chemistry, Innovative Drug Research Center , Shanghai University , Shanghai 200444 , China. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica , Chinese Academy of Sciences , 555 Zuchongzhi Road , Shanghai 201203 , China.
Chen WW
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica , Chinese Academy of Sciences , 555 Zuchongzhi Road , Shanghai 201203 , China.
Gu CX
Department of Chemistry, Innovative Drug Research Center , Shanghai University , Shanghai 200444 , China. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica , Chinese Academy of Sciences , 555 Zuchongzhi Road , Shanghai 201203 , China.
Xu B
Department of Chemistry, Innovative Drug Research Center , Shanghai University , Shanghai 200444 , China.
Xu MH
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica , Chinese Academy of Sciences , 555 Zuchongzhi Road , Shanghai 201203 , China.

Pub Type(s)

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

Language

eng

PubMed ID

29672066

Citation

Liu, Jian-Guo, et al. "Access to Spiroindolines and Spirodihydrobenzofurans Via Pd-Catalyzed Domino Heck Spiroyclization Through C-H Activation and Carbene Insertion." Organic Letters, vol. 20, no. 9, 2018, pp. 2728-2732.
Liu JG, Chen WW, Gu CX, et al. Access to Spiroindolines and Spirodihydrobenzofurans via Pd-Catalyzed Domino Heck Spiroyclization through C-H Activation and Carbene Insertion. Org Lett. 2018;20(9):2728-2732.
Liu, J. G., Chen, W. W., Gu, C. X., Xu, B., & Xu, M. H. (2018). Access to Spiroindolines and Spirodihydrobenzofurans via Pd-Catalyzed Domino Heck Spiroyclization through C-H Activation and Carbene Insertion. Organic Letters, 20(9), 2728-2732. https://doi.org/10.1021/acs.orglett.8b00935
Liu JG, et al. Access to Spiroindolines and Spirodihydrobenzofurans Via Pd-Catalyzed Domino Heck Spiroyclization Through C-H Activation and Carbene Insertion. Org Lett. 2018 05 4;20(9):2728-2732. PubMed PMID: 29672066.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Access to Spiroindolines and Spirodihydrobenzofurans via Pd-Catalyzed Domino Heck Spiroyclization through C-H Activation and Carbene Insertion. AU - Liu,Jian-Guo, AU - Chen,Wen-Wen, AU - Gu,Chang-Xue, AU - Xu,Bin, AU - Xu,Ming-Hua, Y1 - 2018/04/19/ PY - 2018/4/20/pubmed PY - 2018/4/20/medline PY - 2018/4/20/entrez SP - 2728 EP - 2732 JF - Organic letters JO - Org Lett VL - 20 IS - 9 N2 - A new palladium-catalyzed domino approach for the synthesis of attractive spirocyclic indolines and dihydrobenzofurans was developed. The reaction proceeds through a sequential intramolecular Heck spirocyclization, remote C-H activation, and diazocarbonyl carbene insertion. Various spiroindolines and spirodihydrobenzofurans containing two quartenary carbon stereocenters were readily obtained in good to excellent yields. A preliminary study of asymmetric spirocyclization using chiral monophosphoramidite as a ligand was also conducted, enabling access to highly valuable chiral spiroindolines with up to 80% ee. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/29672066/Access_to_Spiroindolines_and_Spirodihydrobenzofurans_via_Pd_Catalyzed_Domino_Heck_Spiroyclization_through_C_H_Activation_and_Carbene_Insertion_ DB - PRIME DP - Unbound Medicine ER -