Literature DB >> 23818095

Diisopinocampheylborane-mediated reductive aldol reactions: highly enantio- and diastereoselective synthesis of syn aldols from N-acryloylmorpholine.

Philippe Nuhant1, Christophe Allais, William R Roush.   

Abstract

Entities:  

Keywords:  aldol reaction; boranes; diastereoselectivity; enantioselectivity; morpholine amides

Mesh：

Substances：

Year:  2013        PMID： 23818095      PMCID： PMC3813003          DOI： 10.1002/anie.201302535

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


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  31 in total

Review 1.  Catalytic asymmetric tandem transformations triggered by conjugate additions.

Authors:  Hong-Chao Guo; Jun-An Ma
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-09       Impact factor: 15.336

2.  Cu(I)-catalyzed reductive aldol cyclizations: diastereo- and enantioselective synthesis of beta-hydroxylactones.

Authors:  Hon Wai Lam; Pekka M Joensuu
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

3.  Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst.

Authors:  Takushi Shiomi; Hisao Nishiyama
Journal:  Org Lett       Date:  2007-03-27       Impact factor: 6.005

4.  Titanium enolates of thiazolidinethione chiral auxiliaries: versatile tools for asymmetric aldol additions.

Authors:  M T Crimmins; K Chaudhary
Journal:  Org Lett       Date:  2000-03-23       Impact factor: 6.005

5.  Dramatic ligand effect in catalytic asymmetric reductive aldol reaction of allenic esters to ketones.

Authors:  Dongbo Zhao; Kounosuke Oisaki; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2006-11-15       Impact factor: 15.419

6.  Sequential reactions promoted by manganese: completely stereoselective synthesis of (E)-alpha,beta-unsaturated amides, ketones, aldehydes, and carboxylic acids.

Authors:  José M Concellón; Humberto Rodríguez-Solla; Pamela Díaz
Journal:  J Org Chem       Date:  2007-09-21       Impact factor: 4.354

7.  CuH-catalyzed enantioselective intramolecular reductive aldol reactions generating three new contiguous asymmetric stereocenters.

Authors:  Bruce H Lipshutz; Benjamin Amorelli; John B Unger
Journal:  J Am Chem Soc       Date:  2008-10-11       Impact factor: 15.419

8.  Borane-mediated aldol cycloreduction of monoenone monoketones: diastereoselective formation of quaternary centers.

Authors:  Ryan R Huddleston; David F Cauble; Michael J Krische
Journal:  J Org Chem       Date:  2003-01-10       Impact factor: 4.354

9.  Stereospecific cyclopropanation of highly substituted C-C double bonds promoted by CrCl2. Stereoselective synthesis of cyclopropanecarboxamides and cyclopropyl ketones.

Authors:  José M Concellón; Humberto Rodríguez-Solla; Carmen Méjica; Elena G Blanco
Journal:  Org Lett       Date:  2007-07-13       Impact factor: 6.005

10.  Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts.

Authors:  Takushi Shiomi; Takahiro Adachi; Jun-ichi Ito; Hisao Nishiyama
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005
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  7 in total

1.  Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors:  Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

2.  (Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: enantioselective synthesis of anti-aldols.

Authors:  Christophe Allais; Philippe Nuhant; William R Roush
Journal:  Org Lett       Date:  2013-07-25       Impact factor: 6.005

3.  Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.

Authors:  Zhiyong Yu; Robert J Ely; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-15       Impact factor: 15.336

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

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

5.  Identification of rapid access to polycyclic systems via a base-catalyzed cascade cyclization reaction and their biological evaluation.

Authors:  Taotao Ling; Victor Hadi; John Bollinger; Fatima Rivas
Journal:  Bioorg Chem       Date:  2020-04-18       Impact factor: 5.275

6.  Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.

Authors:  Jeremy Kister; Daniel H Ess; William R Roush
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005

7.  Confinement-Controlled, Either syn- or anti-Selective Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes.

Authors:  Tynchtyk Amatov; Nobuya Tsuji; Rajat Maji; Lucas Schreyer; Hui Zhou; Markus Leutzsch; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-08-26       Impact factor: 15.419
  7 in total

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