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Enantioselective synthesis of chiral sulfones by Ir-catalyzed asymmetric hydrogenation: a facile approach to the preparation of chiral allylic and homoallylic compounds.
J Am Chem Soc. 2012 Aug 22; 134(33):13592-5.JA

Abstract

A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Bäcklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhou T
Department of Chemistry-BMC, Uppsala University, Box 576, S-75123 Uppsala, Sweden.
Peters B
No affiliation info available
Maldonado MF
No affiliation info available
Govender T
No affiliation info available
Andersson PG
No affiliation info available

MeSH

Allyl CompoundsCatalysisHydrogenationIridiumStereoisomerismSulfones

Pub Type(s)

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

Language

eng

PubMed ID

22835144

Citation

Zhou, Taigang, et al. "Enantioselective Synthesis of Chiral Sulfones By Ir-catalyzed Asymmetric Hydrogenation: a Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds." Journal of the American Chemical Society, vol. 134, no. 33, 2012, pp. 13592-5.
Zhou T, Peters B, Maldonado MF, et al. Enantioselective synthesis of chiral sulfones by Ir-catalyzed asymmetric hydrogenation: a facile approach to the preparation of chiral allylic and homoallylic compounds. J Am Chem Soc. 2012;134(33):13592-5.
Zhou, T., Peters, B., Maldonado, M. F., Govender, T., & Andersson, P. G. (2012). Enantioselective synthesis of chiral sulfones by Ir-catalyzed asymmetric hydrogenation: a facile approach to the preparation of chiral allylic and homoallylic compounds. Journal of the American Chemical Society, 134(33), 13592-5. https://doi.org/10.1021/ja306731u
Zhou T, et al. Enantioselective Synthesis of Chiral Sulfones By Ir-catalyzed Asymmetric Hydrogenation: a Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds. J Am Chem Soc. 2012 Aug 22;134(33):13592-5. PubMed PMID: 22835144.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective synthesis of chiral sulfones by Ir-catalyzed asymmetric hydrogenation: a facile approach to the preparation of chiral allylic and homoallylic compounds. AU - Zhou,Taigang, AU - Peters,Byron, AU - Maldonado,Matías F, AU - Govender,Thavendran, AU - Andersson,Pher G, Y1 - 2012/08/07/ PY - 2012/7/28/entrez PY - 2012/7/28/pubmed PY - 2013/1/9/medline SP - 13592 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 134 IS - 33 N2 - A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Bäcklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%). SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22835144/Enantioselective_synthesis_of_chiral_sulfones_by_Ir_catalyzed_asymmetric_hydrogenation:_a_facile_approach_to_the_preparation_of_chiral_allylic_and_homoallylic_compounds_ L2 - https://doi.org/10.1021/ja306731u DB - PRIME DP - Unbound Medicine ER -