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Enantioselective Access to Spirocyclic Sultams by Chiral Cp(x) -Rhodium(III)-Catalyzed Annulations.
Chemistry. 2016 Feb 12; 22(7):2270-3.C

Abstract

Chiral spirocyclic sultams are a valuable compound class in organic and medicinal chemistry. A rapid entry to this structural motif involves a [3+2] annulation of an N-sulfonyl ketimine and an alkyne. Although the directing-group properties of the imino group for C-H activation have been exploited, the developments of related asymmetric variants have remained very challenging. The use of rhodium(III) complexes equipped with a suitable atropchiral cyclopentadienyl ligand, in conjunction with a carboxylic acid additive, enables an enantioselective and high yielding access to such spirocyclic sultams.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Pham MV
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland.
Cramer N
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland. nicolai.cramer@epfl.ch.

MeSH

Carboxylic AcidsCatalysisHydrogen BondingLigandsMolecular StructureNaphthalenesulfonatesRhodiumSpiro Compounds

Pub Type(s)

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

Language

eng

PubMed ID

26836575

Citation

Pham, Manh V., and Nicolai Cramer. "Enantioselective Access to Spirocyclic Sultams By Chiral Cp(x) -Rhodium(III)-Catalyzed Annulations." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 22, no. 7, 2016, pp. 2270-3.
Pham MV, Cramer N. Enantioselective Access to Spirocyclic Sultams by Chiral Cp(x) -Rhodium(III)-Catalyzed Annulations. Chemistry. 2016;22(7):2270-3.
Pham, M. V., & Cramer, N. (2016). Enantioselective Access to Spirocyclic Sultams by Chiral Cp(x) -Rhodium(III)-Catalyzed Annulations. Chemistry (Weinheim an Der Bergstrasse, Germany), 22(7), 2270-3. https://doi.org/10.1002/chem.201504998
Pham MV, Cramer N. Enantioselective Access to Spirocyclic Sultams By Chiral Cp(x) -Rhodium(III)-Catalyzed Annulations. Chemistry. 2016 Feb 12;22(7):2270-3. PubMed PMID: 26836575.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Access to Spirocyclic Sultams by Chiral Cp(x) -Rhodium(III)-Catalyzed Annulations. AU - Pham,Manh V, AU - Cramer,Nicolai, Y1 - 2016/01/11/ PY - 2015/12/11/received PY - 2016/2/3/entrez PY - 2016/2/3/pubmed PY - 2016/7/7/medline KW - C−H activation KW - asymmetric catalysis KW - chiral Cp ligands KW - rhodium KW - sultams SP - 2270 EP - 3 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 22 IS - 7 N2 - Chiral spirocyclic sultams are a valuable compound class in organic and medicinal chemistry. A rapid entry to this structural motif involves a [3+2] annulation of an N-sulfonyl ketimine and an alkyne. Although the directing-group properties of the imino group for C-H activation have been exploited, the developments of related asymmetric variants have remained very challenging. The use of rhodium(III) complexes equipped with a suitable atropchiral cyclopentadienyl ligand, in conjunction with a carboxylic acid additive, enables an enantioselective and high yielding access to such spirocyclic sultams. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/26836575/Enantioselective_Access_to_Spirocyclic_Sultams_by_Chiral_Cp_x___Rhodium_III__Catalyzed_Annulations_ DB - PRIME DP - Unbound Medicine ER -