Literature DB >> 17298072

Chiral Diphenylprolinol TES ether promoted conjugate addition-aldol-dehydration reactions between alpha,beta-unsaturated aldehydes and 2-N-protected amino benzaldehydes.

Hao Li1, Jian Wang, Hexin Xie, Liansuo Zu, Wei Jiang, Eileen N Duesler, Wei Wang.   

Abstract

A conjugate addition-aldol-dehydration reaction of alpha,beta-unsaturated aldehydes with 2-N-protected amino benzaldehydes has been developed. The process is promoted by (S)-diphenylprolinol TES ether to afford synthetically useful 1,2-dihydroquinolines in high enantioselectivities with good yields. [reaction: see text]

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Year:  2007        PMID： 17298072     DOI： 10.1021/ol062877u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid.

Authors:  Erik C Carlson; Lauren K Rathbone; Hua Yang; Nathan D Collett; Rich G Carter
Journal:  J Org Chem       Date:  2008-06-05       Impact factor: 4.354

2.  Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

Authors:  Xiaojie Lu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Nathan D Collett; Mrinmoy Saha; Rich G Carter
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

4.  Organocatalytic enantioselective β-functionalization of aldehydes by oxidation of enamines and their application in cascade reactions.

Authors:  Shi-Lei Zhang; He-Xin Xie; Jin Zhu; Hao Li; Xin-Shuai Zhang; Jian Li; Wei Wang
Journal:  Nat Commun       Date:  2011       Impact factor: 14.919

5.  Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines.

Authors:  Chittaranjan Bhanja; Satyaban Jena; Sabita Nayak; Seetaram Mohapatra
Journal:  Beilstein J Org Chem       Date:  2012-10-04       Impact factor: 2.883

6.  Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.

Authors:  Zhi-Cong Geng; Jian Chen; Ning Li; Xiao-Fei Huang; Yong Zhang; Ya-Wen Zhang; Xing-Wang Wang
Journal:  Beilstein J Org Chem       Date:  2012-10-09       Impact factor: 2.883
  6 in total

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