Pd-Catalyzed umpolung asymmetric allylic alkylation of hydrazones to vicinal tertiary and quaternary chiral carbon centers

Author:

Huang Shuai1,Zhang Gao-Peng1,Jiang Yang-Jie1,Yu Fei-Le1,Ding Chang-Hua2ORCID,Hou Xue-Long13ORCID

Affiliation:

1. State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, China

2. Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China

3. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, SIOC, CAS, China

Abstract

Vicinal tertiary and quaternary chiral carbon centers are constructed with high regio-, diastereo- and enantioselectivities via Pd-catalyzed umpolung asymmetric allylic alkylation of hydrazones with monosubstituted allyl reagents by using Kündig type chiral N-heterocyclic carbene as the ligand.

Funder

Chinese Academy of Sciences

National Natural Science Foundation of China

Science and Technology Commission of Shanghai Municipality

Croucher Foundation

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Reference48 articles.

1. A.Pfaltz and M.Lautens , in Comprehensive Asymmetric Catalysis , ed. E. N. Jacobsen , A. Pfaltz and H. Yamamoto , Springer-Verlag , Berlin , 1999 , pp. 833–886

2. C.-H.Ding and X.-L.Hou , in Comprehensive Organic Synthesis , ed. G. A. Molander and P. Knochel , Elsevier , Oxford , 2nd edn, 2014 , vol. 4, pp. 648–698

3. Stereochemistry of nucleophilic attack on π-allylpalladium complexes. Evidence for cis-migration of acetate from palladium to carbon

4. The Fate of Bis(η3-allyl)palladium Complexes in the Presence of Aldehydes (or Imines) and Allylic Chlorides: Stille Coupling versus Allylation of Aldehydes (or Imines)

5. Intramolecular Coupling of Allyl Carboxylates with Allyl Stannanes and Allyl Silanes: A New Type of Reductive Elimination Reaction?

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