Literature DB >> 29799203

Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones.

Sheng-Biao Tang1, Xiao Zhang1, Hang-Fei Tu1, Shu-Li You1,2.   

Abstract

Highly regio- and enantioselective rhodium-catalyzed allylic alkylation of 1,3-diketones with racemic secondary allylic alcohols is reported. In the presence of a Rh-catalyst derived from the Carreira (P, olefin)-ligand and TFA as an additive, chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with excellent regio- and enantioselectivity ( b/ l > 19/1, 86-98% ee). The direct utilization of allyl alcohols as electrophiles represents an improvement from the viewpoint of an atom economy. Both aryl- and aliphatic-substituted allyl alcohols are suitable substrates with excellent reaction outcomes. This reaction features mild conditions, broad substrate scope, and readily available substrates.

Entities:  

Year:  2018        PMID: 29799203     DOI: 10.1021/jacs.8b05126

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[b]thiophenes.

Authors:  Christopher Cunningham; Matthew Cloyd; Aimee Phillips; Soha Khan; Katherine Whalen; Tanay Kesharwani
Journal:  Org Biomol Chem       Date:  2021-05-12       Impact factor: 3.876

2.  Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination.

Authors:  He-Yuan Bai; Fu-Xin Tan; Tuan-Qing Liu; Guo-Dong Zhu; Jin-Miao Tian; Tong-Mei Ding; Zhi-Min Chen; Shu-Yu Zhang
Journal:  Nat Commun       Date:  2019-07-11       Impact factor: 14.919

3.  Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.

Authors:  Sangjune Park; Nathan J Adamson; Steven J Malcolmson
Journal:  Chem Sci       Date:  2019-04-17       Impact factor: 9.825

4.  Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(iii) compound.

Authors:  Mohan Chandra Sau; Smita Mandal; Manish Bhattacharjee
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

5.  Intensification of Double Kinetic Resolution of Chiral Amines and Alcohols via Chemoselective Formation of a Carbonate-Enzyme Intermediate.

Authors:  Jan Samsonowicz-Górski; Anna Brodzka; Ryszard Ostaszewski; Dominik Koszelewski
Journal:  Molecules       Date:  2022-07-06       Impact factor: 4.927

  5 in total

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