Literature DB >> 32191438

Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Cole C Meyer1, Eliezer Ortiz1, Michael J Krische1.   

Abstract

Catalytic reductive coupling of enone, acrylate, or vinyl heteroaromatic pronucleophiles with carbonyl or imine partners offers an alternative to base-mediated enolization in aldol- and Mannich-type reactions. In this review, direct catalytic reductive aldol and Mannich reactions are exhaustively catalogued on the basis of metal or organocatalyst. Stepwise processes involving enone conjugate reduction to form discrete enol or (metallo)enolate derivatives followed by introduction of carbonyl or imine electrophiles and aldol reactions initiated via enone conjugate addition are not covered.

Entities:  

Year:  2020        PMID： 32191438      PMCID： PMC7904107          DOI： 10.1021/acs.chemrev.0c00053

Source DB:  PubMed          Journal:  Chem Rev        ISSN： 0009-2665            Impact factor:   60.622


  153 in total

1.  Tandem enantioselective conjugate addition: electrophile trapping reactions. Application in the formation of syn or anti aldols.

Authors:  A Alexakis; G P Trevitt; G Bernardinelli
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

2.  Rhodium-catalyzed reductive aldol reactions using aldehydes as the stoichiometric reductants.

Authors:  Michael C Willis; Robert L Woodward
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

3.  Asymmetric induction in hydrogen-mediated reductive aldol additions to alpha-amino aldehydes catalyzed by rhodium: selective formation of syn-stereotriads directed by intramolecular hydrogen-bonding.

Authors:  Cheol-Kyu Jung; Michael J Krische
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

4.  Aromatic heterocycles as activating groups for asymmetric conjugate addition reactions. Enantioselective copper-catalyzed reduction of 2-alkenylheteroarenes.

Authors:  Leszek Rupnicki; Aakarsh Saxena; Hon Wai Lam
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

5.  Asymmetric Induction at Remote Quaternary Centers of Cyclohexadienones by Rhodium-Catalyzed Conjugate Hydrosilylation.

Authors:  Yuki Naganawa; Mayu Kawagishi; Jun-Ichi Ito; Hisao Nishiyama
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-21       Impact factor: 15.336

6.  A new entry to Pd-H chemistry: catalytic asymmetric conjugate reduction of enones with EtOH and a highly enantioselective synthesis of warfarin.

Authors:  Yasunori Tsuchiya; Yoshitaka Hamashima; Mikiko Sodeoka
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

Review 7.  Nickel-catalyzed intermolecular domino reactions.

Authors:  S Ikeda
Journal:  Acc Chem Res       Date:  2000-08       Impact factor: 22.384

8.  Copper-catalyzed tandem conjugate addition-electrophilic trapping: ketones, esters, and nitriles as terminal electrophiles.

Authors:  Kyriacos Agapiou; David F Cauble; Michael J Krische
Journal:  J Am Chem Soc       Date:  2004-04-14       Impact factor: 15.419

9.  Rhodium-catalyzed approach to Mannich-type products using aldimine, alpha,beta-unsaturated ester, and hydrosilane.

Authors:  Takako Muraoka; Shin-ichi Kamiya; Isamu Matsuda; Kenji Itoh
Journal:  Chem Commun (Camb)       Date:  2002-06-21       Impact factor: 6.222

10.  Multiple reaction pathways in rhodium-catalyzed hydrosilylations of ketones.

Authors:  Nathanaëlle Schneider; Markus Finger; Christian Haferkemper; Stéphane Bellemin-Laponnaz; Peter Hofmann; Lutz H Gade
Journal:  Chemistry       Date:  2009-11-02       Impact factor: 5.236
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  6 in total

1.  Photochemical single-step synthesis of β-amino acid derivatives from alkenes and (hetero)arenes.

Authors:  Guangying Tan; Mowpriya Das; Hyeyun Keum; Peter Bellotti; Constantin Daniliuc; Frank Glorius
Journal:  Nat Chem       Date:  2022-08-01       Impact factor: 24.274

2.  Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl-Cu Species.

Authors:  Yuyang Dong; Alexander W Schuppe; Binh Khanh Mai; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2022-03-26       Impact factor: 16.383

3.  Hf(OTf)4-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones.

Authors:  Zhen-Zhen Chen; Dong-Zhao Yang; Ying-Ying Dong; Mei Chi; Shou-Zhi Pu; Qi Sun
Journal:  Molecules       Date:  2022-02-08       Impact factor: 4.411

4.  Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents.

Authors:  Petr Oeser; Jakub Koudelka; Hana Dvořáková; Tomáš Tobrman
Journal:  RSC Adv       Date:  2020-09-22       Impact factor: 4.036

5.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084

Review 6.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020
  6 in total

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