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Lewis base assisted Brønsted base catalysis: direct regioselective asymmetric vinylogous alkylation of allylic sulfones.
Chemistry. 2011 Aug 16; 17(34):9489-93.C

Abstract

A Lewis base assisted Brønsted base catalysis (LBABB) strategy is applied for direct asymmetric vinylogous alkylation of allylic sulfones with Morita-Baylis-Hillman (MBH) carbonates, in which a strong Brønsted base, tert-butoxy anion, generated in situ from a tertiary amine catalyst and MBH carbonate, is crucial in activating unstabilized nucleophiles. The γ-regioselective alkylation products were obtained with good to excellent enantiomeric excess values when catalyzed by a modified cinchona alkaloid.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Jiang L
Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, PR China.
Lei Q
No affiliation info available
Huang X
No affiliation info available
Cui HL
No affiliation info available
Zhou X
No affiliation info available
Chen YC
No affiliation info available

MeSH

AlkylationAllyl CompoundsCarbonatesCatalysisChemistry, OrganicCinchona AlkaloidsLewis BasesMagnetic Resonance SpectroscopyMolecular StructureOxidesPrescription DrugsStereoisomerismSulfones

Pub Type(s)

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

Language

eng

PubMed ID

21721059

Citation

Jiang, Lin, et al. "Lewis Base Assisted Brønsted Base Catalysis: Direct Regioselective Asymmetric Vinylogous Alkylation of Allylic Sulfones." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 17, no. 34, 2011, pp. 9489-93.
Jiang L, Lei Q, Huang X, et al. Lewis base assisted Brønsted base catalysis: direct regioselective asymmetric vinylogous alkylation of allylic sulfones. Chemistry. 2011;17(34):9489-93.
Jiang, L., Lei, Q., Huang, X., Cui, H. L., Zhou, X., & Chen, Y. C. (2011). Lewis base assisted Brønsted base catalysis: direct regioselective asymmetric vinylogous alkylation of allylic sulfones. Chemistry (Weinheim an Der Bergstrasse, Germany), 17(34), 9489-93. https://doi.org/10.1002/chem.201100534
Jiang L, et al. Lewis Base Assisted Brønsted Base Catalysis: Direct Regioselective Asymmetric Vinylogous Alkylation of Allylic Sulfones. Chemistry. 2011 Aug 16;17(34):9489-93. PubMed PMID: 21721059.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis base assisted Brønsted base catalysis: direct regioselective asymmetric vinylogous alkylation of allylic sulfones. AU - Jiang,Lin, AU - Lei,Qian, AU - Huang,Xin, AU - Cui,Hai-Lei, AU - Zhou,Xue, AU - Chen,Ying-Chun, Y1 - 2011/06/30/ PY - 2011/02/17/received PY - 2011/7/2/entrez PY - 2011/7/2/pubmed PY - 2011/12/13/medline SP - 9489 EP - 93 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 17 IS - 34 N2 - A Lewis base assisted Brønsted base catalysis (LBABB) strategy is applied for direct asymmetric vinylogous alkylation of allylic sulfones with Morita-Baylis-Hillman (MBH) carbonates, in which a strong Brønsted base, tert-butoxy anion, generated in situ from a tertiary amine catalyst and MBH carbonate, is crucial in activating unstabilized nucleophiles. The γ-regioselective alkylation products were obtained with good to excellent enantiomeric excess values when catalyzed by a modified cinchona alkaloid. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/21721059/Lewis_base_assisted_Brønsted_base_catalysis:_direct_regioselective_asymmetric_vinylogous_alkylation_of_allylic_sulfones_ L2 - https://doi.org/10.1002/chem.201100534 DB - PRIME DP - Unbound Medicine ER -